Evan your point about wholesaling is a good one too, I have to admit the red flags did go off for me a bit but I figured it'd be worth seeing what others had to say.

We can split hairs all we want and not like the outcome but he fact remains the house was held red the senate flipped red and the presidency is red.

What are some red flags I may be missing in evaluating this?

You can't rent out a PO box and live there.And yea that sounds like a huge red flag to me. 

That is a thought that's in the back of my mind regarding all the red tape you may encounter on the building side.

This California law eliminates much of the red tape by bypassing environmental reviews and subjective local approvals, creating a faster and more predictable development process.

After 20+ years in real estate partnerships, here's what actually puts you on the IRS radar (and what doesn't):REAL Red Flags That Matter:The Partner Complaint TriggerDisgruntled partner files Form 8082K-1 disputesPartnership disputes leading to tax filingsReal Impact: Instant IRS attentionSuspicious Loss ClaimsLosses exceeding investmentArtificial basis inflationSudden large losses without economic realityExample: $100K investment claiming $500K lossesRelated Party GamesCircular property flipsBelow-market transfersFamily partnership schemes without substanceWatch Out: IRC §267 and §707(b) violationsDebt Engineering Red FlagsBasis inflation schemesArtificial guarantee arrangementsPartner debt shifts near year-endCritical: IRC §752 compliance matters!

@Juliann MoralaA GC is suitable for estimating rehab costs, but consider hiring a property manager or investor-friendly realtor for unbiased opinions.Video Walkthrough – Have them record a wide-angle video of the interior and exterior to capture the whole condition.Floor Plan Mapping – Use an app like MagicPlan to create a detailed floor plan with measurements.Major Systems Check – Roof, foundation, HVAC, plumbing, and electrical—any red flags?

That was a huge red flag for me.  

Depending on the fee schedule and activity this can cost significant transaction fees and always includes some red tape and extra processes to go through.