Quote from @Rohullah Sharifi: Short-term rental (STR) activities require active participation and proper documentation to substantiate your involvement.

Here’s a quick shortlist that fits your needs (3 doors):Stessa - built for small portfolios; auto-tracks income/expenses and lets you scan receipts via the mobile app.Hemlane - end-to-end PM: leasing, online rent, maintenance, accounting; good if you want workflows plus optional local agent help. hemlane.comBuildium - more robust if you plan to scale; solid accounting and document storage/e-sign for leases and notices.DoorLoop - all-in-one with straightforward pricing as you add units.

Quote from @Heidi Christensen: What documents do you absolutely insist on when structuring a seller-finance deal?

The STR tax strategy is most beneficial for high-income earners (think: $300K+ annual household income). 

I realize that I need to get some documents from my GC and have him sign some contracts before we start officially working together but want to make sure I'm not forgetting anything that might put me in a bad situation. 

Aligning with your property manager and building a strong relationship could be beneficial.

You spend 100 hours, and nobody else (contractors, cleaners, property managers) spend more hours than you doThe hours have to be documented, and they have to be actual work specific to STRs.

The Registered Agent will record the documents on your behalf so only their name and information appear on the documents.

To make it fast and easy, decided to use Furnish Finders - Keycheck Documents for setting up the NYS lease.

I believe the best app to document is REPStracker.