The quick test is rent minus the main payment minus the line payment minus a repairs cushion and if that number is thin it gets tight fast.

You may want multiple year of tax returns so that you can average out the income. 

"Would you say that looking back, going through the legwork of establishing a Reg D entity was worthwhile for you on that deal in comparison to just establishing a basic LLC structure with multiple members?"

If you are listed on multiple platforms and need a more robust solution, consider PMPs like Guesty, Hostfully (which I use), Hostaway, etc., to manage your guest messaging and get the bookkeeping capabilities. 

Multiple tenants = multiple income streams - this is ideal to combat vacancies.

Multiple enforcement paths.

I think you need to test 5 different things for your market to see what happens.

I finally found a property that will cashflow, im in the middle of getting multiple quotes for the rehab work that needs to be done.  

Curious how other investors stay on top of deadlines once deals start stacking up.I’ve been seeing a lot of newer investors juggle contracts, addenda, and lender requests all at once — especially when running multiple deals.What systems or processes are you using to keep files clean and closings smooth?

You’ll likely never find the perfect deal or perfect funding but if you can find opportunities that check multiple boxes, in my opinion it’s best to just make the first move and learn through experience.