For example in many jurisdictions I can STR units in a duplex but cannot STR an ADU (some jurisdictions will let you STR if you owner occupy).

Same owners, same management (self managed), both STRs.

I'll be an owner-occupied landlord with a long-term tenant next door. 

@Tom CarmodyI would recommend getting in touch with owners in the particular hotel you’re wanting to buy in and ask them how they like it and how much they are really making & any issues with the hotel.

Ask to speak with some of their current owners and current/former tenants.

To stretch your $35,000, consider a FHA Loan (3.5% down) or owner financing.

I use Auto Owners Insurance.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I'm looking at a duplex and id owner occupy it .

You especially need one side empty for any owner occupant buyers.