To add additional context,  I would personally be more willing to sign my name onto a $6M mortgage collateralized against a $10M asset in an "A" market that has historically low vacancy rates, no deferred maintenance and is located in a stable market with a rent roll that covers the debt services and operating expenses with reasonable cushion for reserves than sign my name on a $90,000 loan collateralized against a $100K property in a C/D unstable market with high vacancy rates and where capex will disproportionately impact operations.

Great guy and excellent operator with great results.

You don't want to bring over poor operations to STR because you will also fail there.

Other syndiicators are not good operators. 

They may seem attractive on a spreadsheet if you are chasing cash flow, but the fundamentals are not as strong and these properties are  disproportionately impacted by capex and operating costs.

I will be managing all booking, renovation, and maintenance operations of the STR (besides mandatory front desk operations, and cleaning - required to be run by the Hotel).

My spouse and I didn’t learn our lesson here and took on a second partner in a real estate/restaurant operation and ended up again having to have legal action to sever the partnership when it failed.

In the middle of buying out partner (50:50 partnership) in a mixed-use owner operated Gas station and real estate property.

Analyze deals like a pro using the 1% rule and understand operating expenses before making an offer.

@Jennifer Taylor First  answer this: Do you currently operate your properties with all proper permits and licenses?