A repeatable diligence process matters more than any single deal or personality.

To me it seems like a situation where I could get repeat business if I was the one agent that would take it on.

I like that you’re thinking about blending personal use with income and long-term appreciation instead of just chasing short-term cash flow.If you structure it right from the beginning, that first one can become the blueprint for the rest of the portfolio.I’m based in Florida and work with a lot of investors doing STR/MTR and Gulf Coast properties, so happy to share insights anytime as you refine your strategy.Thanks Jonathan, I'm a systems and processes guy so I love the idea of making the first one a repeatable blueprint.

Because the Property Class dictates the Class of the tenant pool that the property will attract.The Tenant Class greatly impacts rental income stability and property maintenance/damage by tenants.Both Property Class and Tenant Class will affect what type of contractors, handymen and property management companies you should target and be willing to deal with a property.The Property Class will also impact the maintenance & renovations you do to, “Maintain to the Neighborhood”.Why is that important?

Pick a clear service list, set fair flat pricing where possible, and focus on repeat investors, not one off jobs.

RECOMMENDATION - Clear GO/NO-GO with specific reasoning - If GO: Key value drivers and execution priorities - If NO-GO: What would need to change for deal to work - Due diligence action items TARGET CRITERIA: - Markets: TN, KY, FL preferred (pro-landlord states) - B and C+ class neighborhoods preferred (A class = lower returns, D class = higher risk) - Value-add opportunities through renovation and rent growth - Conservative underwriting with realistic expense assumptions - Cash flow target: Varies by deal size - provide actual monthly cash flow projection (Note: Portfolio approach may combine multiple smaller deals to reach aggregate targets) CASH FLOW PRESENTATION: - Always show: Monthly cash flow at stabilization - Always show: Annual cash-on-cash return % - Let the numbers speak - no arbitrary minimums per deal - Flag if deal is cash flow negative or marginal (<$2,000/month) OUTPUT STYLE: - Lead with executive summary: property class, neighborhood grade, and recommendation - Present demographic data in clear tables - Show all financial assumptions and calculations - Be direct about weaknesses - crime, poverty, or demographic concerns that affect risk - Flag if neighborhood quality doesn't align with investment criteria - Provide specific action items for due diligence RESEARCH APPROACH: - Use web search to gather current crime statistics, census data, and economic indicators - Cross-reference multiple sources for demographic accuracy - Compare area metrics to county/state/national averages for context - Identify trends (improving vs. declining neighborhoods)Is anybody else using something similar to do a quick vetting of deals? 

Here’s a full, distilled synthesis that pulls together all 13 responses + the final long one, with extra focus on what people repeatedly agreed on and what showed up most often.Executive Summary (One-Page Takeaway)There is overwhelming consensus that:Normal wear and tear is expected, unavoidable, and not chargeableSecurity deposits should only be used for clear, provable damageBorderline deductions are almost never worth the conflictThe standard is not “what technically could be charged,” but “what you’d confidently defend to a judge”Most experienced landlords and PMs favor a conservative, documentation-heavy, expectation-setting approach that prioritizes fairness, consistency, and dispute avoidance over maximizing deposit recovery.The Strongest Areas of Agreement (Mentioned Repeatedly)1.

Functional gets 5 stars and repeat bookings.

If remote work trends accelerate or ACE train ridership drops, that affects both appreciation and tenant demand.

What can be overwhelming is that often AI will give you a portion of what it is that you need, but it tends to make suggestions that can take you down a rabbit hole and then next thing you know, you've wasted hours and still haven't crafted anything useful.I am mentioning this because it sounds like you're asking for prompts but I think what you're actually trying to tackle is designing a repeatable analysis system that AI plugs into.Instead of one giant prompt, try building these three prompts instead: a) a fixed analysis framework prompt (define how AI should think, calculate and structure outputs.