AI Advisor

Your REP Documentation,
Reviewed Before the IRS Does

REPSShield's AI Advisor is not a chatbot. It reads your actual time log, cites specific IRS regulations and Tax Court cases, and runs your documentation through the same 12-check framework IRS examiners use — so you find the gaps before the audit does.

14-day free trial · No credit card required · All AI modes included

Three Modes

One Advisor, Three Operating Modes

Different tasks require different tools. REPSShield routes your query to the right mode automatically — or you can select the mode directly.

Quick Mode

Conversational Time Entry

Describe what you did in plain language. The AI converts it to a structured IRS-compliant time entry — property, activity type, hours, and description — before your contemporaneous window closes.

  • Recognizes 30 qualifying activity types
  • Matches your property by name or address
  • Shows a preview card before committing the entry
  • Creates server-side contemporaneous timestamp
Advisor Mode

Citation-Backed Tax Guidance

Ask any REP status question. Answers draw from 282 curated documents — IRS publications, Treasury Regulations, and Tax Court cases — with inline citation chips identifying the exact source.

  • 282-document IRS and Tax Court knowledge base
  • Specific citations: Treas. Reg. 1.469-9, Pub. 925, and more
  • Applies rules to your specific filing situation
  • Supplements with current IRS.gov guidance when relevant
Compliance Mode

See Through an Examiner's Eyes

Runs your time log through the IRS Passive Activity Loss Audit Technique Guide's 12 audit checks. Produces a pass/warning/flag compliance report you can download as a PDF before you file.

  • Follows the IRS examiner's actual review framework
  • 12 discrete checks across your full log
  • Each flag includes a specific remediation action
  • Downloadable PDF compliance report
Quick Mode

Log Time in One Sentence

The moment after a site visit or contractor call is when contemporaneous documentation has the most value — and the highest friction. Quick Mode removes that friction. Describe what you did and the AI handles the rest.

  • 30 recognized activity types

    Including distinctions the IRS cares about: "contractor oversight" versus "direct construction," "tenant acquisition" versus "tenant management."

  • Contemporaneous timestamp

    The server records the creation time the moment you confirm the entry — not when you opened the app.

  • Always a preview before committing

    Every entry shows a confirmation card with all five fields so you can correct before saving.

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Advisor Mode

Every Answer Cites the Source

REP status questions have specific answers grounded in Treasury Regulations and Tax Court precedent. Advisor mode retrieves from a 282-document knowledge base — not general training data — and shows you exactly which regulation or case it relied on.

Knowledge base contents

  • IRS Publications 527, 925, and 946
  • Treasury Regulations 1.469-1 through 1.469-11
  • IRS Passive Activity Loss Audit Technique Guide
  • Tax Court memoranda and opinions through early 2026
  • Chief Counsel Advice memoranda on material participation
  • Revenue Procedures on late elections and corrections

Citation chips on every answer

Inline markers identify each source — "Treas. Reg. 1.469-9(b)(4) · Knowledge Base" or "Mirch v. Commissioner, T.C. Memo 2025-18 · Knowledge Base" — so you can bring the exact citation to your accountant.

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Compliance Mode

The 12-Check Audit Engine

Compliance mode follows the IRS Passive Activity Loss Audit Technique Guide — the actual document IRS examiners use when reviewing REP status claims. It runs 12 discrete checks against your time log, then produces a pass/warning/flag report you can download before you file.

01

Contemporaneous logging pattern

Analyzes the gap between activity dates and entry creation timestamps. Entries created within 24 hours are strongest. Multi-day lag patterns are flagged.

02

Rounded hours detection

Flags logs where every entry is exactly 1, 2, 3, or 4 hours — a documented IRS audit red flag referenced in the Passive Activity Loss Audit Technique Guide.

03

Duration plausibility

Cross-references logged duration against activity type and property. An 8-hour "tenant screening" entry for a single-unit property triggers a flag.

04

Activity eligibility verification

Each entry's activity type is checked against the IRS qualifying activity taxonomy. Investment analysis, education, and general research are non-qualifying and excluded.

05

Evidence presence

Identifies high-value entries — large hour blocks, heavily audited activity types — that lack attached corroborating documentation.

06

Material participation test application

Verifies you are relying on the correct test per property. Claims under Test 3 (100 hours, more than anyone else) are flagged when a full-service property manager is present.

07

On-call time analysis

Flags entries that appear to claim passive on-call or availability time as qualifying hours. The IRS requires that actual services were rendered.

08

Travel time attribution

Verifies that travel time entries are linked to a destination property and a qualifying activity. Unlinked travel claims are a common audit adjustment.

09

Pattern consistency across tax year

Identifies months with zero entries, implausibly high months, or large gaps followed by catch-up logging — patterns inconsistent with active management.

10

Short-term rental path analysis

For STR properties, applies the 500-hour and 100-hour material participation tests separately and flags properties where claimed losses may not be supportable.

11

50% test verification

Calculates qualifying real estate hours against your documented non-real-estate professional time and flags if the more-than-half-time test appears at risk.

12

Grouping election consistency

If you have made a grouping election, verifies that material participation is applied to the grouped activity and flags properties added after the election without an amendment.

Compliance Report Output

Each check returns a status, a finding, and a fix

The downloadable PDF shows every check as Pass, Warning, or Flag — with the specific issue identified and a recommended remediation action. Bring it to your CPA before filing or use it as an internal pre-audit checklist.

Contemporaneous logging Pass
Rounded hours detected Warning
3 entries missing evidence Flag
Travel time attribution Pass
50% test verified Pass
Logging gap — February Warning

12 checks · Downloadable PDF

Session Memory

It Remembers Your Situation

REPSShield builds a persistent tax profile — filing status, employment type, property count, property manager usage, grouping elections, and more. Every AI interaction applies to your actual situation, not a generic one.

Your 19-step tax profile

An interactive questionnaire establishes your filing situation once. Every Advisor and Compliance mode answer is personalized against it.

Cross-session continuity

Start a new conversation and the AI already knows your properties, your current-year hours, and what you discussed recently. No re-explaining.

12-month conversation history

Conversations are stored and searchable. Auto-generated titles — "Material participation test for Oak Street STR" — let you find old threads fast.

Smart Query Routing

Simple questions — "what is the 750-hour rule?" — route to a fast model and return in under two seconds. Complex multi-property, multi-test questions route to extended analysis automatically. The UI surfaces the routing decision so you always know the depth of analysis you are getting.

  • Automatic routing based on question complexity
  • Simple questions answered in under 2 seconds
  • Override to request enhanced analysis on any query

Pushback Mode

Opt-in mode that inverts the AI's posture. Instead of explaining requirements and flagging gaps, it acts as a constructive adversary — raising the objections an IRS examiner would raise against your specific entries. Use it before filing to find weaknesses before the audit does.

  • Opt-in, session-level — turn on when you want a stress test
  • Reviews your actual logged entries, not hypotheticals
  • Flags vague descriptions, misclassified types, weak evidence

Frequently Asked Questions

How is REPSShield's AI Advisor different from a generic AI chatbot?
A generic AI chatbot answers questions from its training data with no access to your time log, your property portfolio, or current IRS guidance. REPSShield's AI Advisor reads your actual records, cites specific Treasury Regulations and Tax Court cases by name, and runs checks against your documentation before you file. It also remembers your situation across conversations — so you never re-explain your filing status, property count, or prior questions.
What is the 12-check compliance engine and when should I run it?
The 12-check compliance engine evaluates your time log against the same framework described in the IRS Passive Activity Loss Audit Technique Guide — the document IRS examiners use when reviewing REP status claims. It checks for rounded hour patterns, documentation gaps, travel time attribution errors, on-call time misuse, material participation test misapplication, and more. Run it at mid-year to catch problems early, and again before filing to confirm your position before your CPA submits the return.
What regulations and cases does the AI cite in its answers?
Advisor mode draws from a curated knowledge base of 282 documents: IRS Publications 527, 925, and 946; Treasury Regulations 1.469-1 through 1.469-11; IRC Sections 469, 168, and 1231; the IRS Passive Activity Loss Audit Technique Guide; Chief Counsel Advice memoranda; and Tax Court memoranda and opinions through early 2026. Every answer that relies on a specific document includes a citation chip identifying the source — so you can bring the exact regulation or case to your accountant.
What is Quick Mode and how does it create time entries?
Quick Mode lets you describe what you did in plain language and the AI converts it into a structured time entry. You might say "I spent two hours at my Oak Street property dealing with the HVAC contractor this morning." The AI identifies the property, selects the correct IRS activity type (construction/improvement oversight), sets the date and hours, and shows you a preview card before creating the entry. It recognizes 30 qualifying activity types — including distinctions like contractor oversight versus direct construction work — so each entry is correctly categorized the first time.
Does the AI remember what we discussed in previous sessions?
Yes. REPSShield stores your conversation history and your 19-step tax profile persistently across sessions. When you start a new conversation the AI already knows your filing status, property count, whether you use a property manager, your current-year hour totals, and what you discussed recently. You never re-explain your situation.
What is Compliance Mode and how does it differ from Advisor Mode?
Advisor mode answers your questions about REP rules and regulations — you ask, it explains, with citations. Compliance mode flips the direction: it proactively reviews your documentation the way an IRS examiner would and tells you what it finds. Where Advisor mode is reactive, Compliance mode is an active audit simulation against your real data. The two modes complement each other: use Advisor mode to understand the rules, use Compliance mode to confirm your log satisfies them.
Can the AI tell me if my specific entries will hold up in an audit?
The 12-check compliance engine can flag entries that are likely to be scrutinized — those with rounded hours, vague descriptions, missing evidence, or activity types the IRS does not recognize as qualifying. It also includes an optional Pushback Mode that stress-tests your entries by raising the objections an IRS examiner would raise. This is not a guarantee of any audit outcome, but it is the most rigorous pre-filing review available short of hiring a tax attorney.
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