However, I remember the process of onboarding my properties being a nightmare back in 2020 and would rather just keep my current mediocre manager than deal with a whole new nightmare and still risk them being not good. 

Seems like a high-risk, low reward situation though.

Is it worth it to go through the proper process with the city and run the risk of a huge expense to make this a 3rd unit? 

I personally wouldnt - I am sure you could use the equity to get more than $600/month in cash flow however that would possibly require some work and risk on yalls end.

I get FinTech is a high-risk activity, but imagine the industry will consolidate to one or a few strong players.

.- Put Upward pressure on real estate operating costs: Increased costs for raw materials and supplies, and the likely increased costs for labor involved in many real estate related CapEx and maintenance projects signal the risk of increase in costs for real estate operators.If there is no impact on near-term supply, a modest slowing of inbound (illegal) migration, more reason to believe that the cost of many goods and services will increase, and real reason to believe that inflation triggered by something other than an increase in the money supply (namely the cost of specific goods and services that are NOT housing going up, which comprise the CPI) will force the Fed to raise rates, this, on the whole, is not good for real estate investment returns. 

STRs are a great way to make money, that's for sure...but it does not come without risk.

The Homeowners Insurance will include Builder's Risk. 

There is a profit but not worth the risk.  

I plan to refinance in two to three year once rates come down a bit.That said, I need to be very confident in my numbers on the hotel, since I'm putting risk on my other properties and essentially wiping out their cash flow.Happy to connect.