If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

This will be my first investment property and I am hesitant to just hand $30k+ to someone and trust it'll all work out.

Aloha,Given that this is the first month using the Avail system, unless you specifically provided the tenant in advance with information on the lag time from first hand experience, I would let it go and simply inform them of how the timing did not work out, and have them adjust their "pay" date accordingly, reminding them of the "late" date and penalty for future payments.

Covid mortgage workout programs are still in effect and not sunsetting until April 2025, unless they extend...again.

If STRs don’t work out, you can still sell at a profit.

Some just try to fake an answer, but you can tell who is honestly surprised and the  they start talking about their cleaning routines

Geez  I would be talking to your HML right now as I doubt they want to take it over.and try to get a workout with them ASAP.. sounds like its going to be  a loss anyway you cut it and I have to think you put up cash for a down payment as well. maybe someone else will have some pearls for you.Wholesaler is going to low ball you for sure.

Did you use a calculator or spreadsheet, or did you simply work out the math like rental income minus PITI, 8% for CapEx, 8% for vacancy, and 5% for repairs?

Right team, right attitude, right maintenance can make some tough assets work out.

Seems to work out great for me.