@Jason Dubon I use a percentage of the rental income to prepare for expenses.

Whether you’re offering services, partnering on projects, or exploring your own investments, leverage your expertise to identify undervalued properties and add value.

Utilities are OFTEN overlooked so reach out to power, telecom, gas (or go all electric), water, and sewer to make sure you understand what it would take to get separately metered services from the primary house.

Very good resource for getting set up with STR property managers, cleaning services, realtors, lenders, etc. https://www.getchalet.com/

Quote from @Nadine Wallace: You can do simplisafe with/without Wi-Fi, but you will need cellular service.

Quote from @Jeffrey Hill: There are a couple of challenges with financing the difference. 1) The current servicer has to approve it. 2) Finding a lender to do a 2nd mortgage at 100% CLTV is almost impossible.

The cash value in the policy service as collateral for the loan.

I've had some not happy when I have asked them to split it out.I've tried asking questions to the IRS customer service reps, and didn't have the best luck.While I cannot cite a specific official guidance on this issue, I consider debit cards exempt.

Not every STR has to be a 4 Seasons and even those I've waited on service before and it's not like someone was breathing down their neck waiting to revoke their hotel license when it happened. 

I've seen folks charge as high as $5,000 to $10,000 for tax planning and tax preparation, But i also know high quality folks that have fees are around $1,200 to 2k.