I get where some people could do it in an odd way that throws off red flags.

Id also throw in some photos of the school or mascot in your str listing. maybe even a flag of the mascot in your listing. 

@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?

I can kind of understand that he wants to make sure I'm legit but that's a bit of a red flag for me.

*Any red flags unique to the Pittsburgh market.I’m also hoping to connect with fellow investors, agents, or property managers who are familiar with the local market.

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

Some carriers won't allow insured to be a trust, so in that case do it in your company name with trust as additional insured.

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

If so, is there any red flags such as rental restrictions, limitations, etc.

•If a lot of homes are listed but few are leasing, that’s a red flag.