These things need so much power that unless the site has access to major grid access point you're wasting your time. 

Losing money? 

I am very aware of the fact that it is overall a losing game, but I have to work on my psychology on this.  

The trade-off is losing out on potential growth from a reinvested 1031 exchange, but if you’re thinking about a HELOC later to invest again, this could bridge the gap.What I’d do in your shoes:If it were me, I’d run the numbers on a worst-case scenario for each option.

If you can rehab your way into a house-hack of a small multifamily and live on site, I think that would allow you to improve your cash flow by getting a short-term rental license even though the city is making it harder to do STRs.

It is also risky when you consider that if you lose, you do not get reimbursed for legal fees.If you feel that you will win rather quickly, why not represent yourself?

Quote from @Stetson Oates: The vast majority of disputes are over security deposits and the most a landlord could lose is 3x the deposit amount.Slip-and-fall or other major lawsuits almost never happen.

quickest way to lose your license is trust fund violations.

I read on JP Morgan Chase's site that they could do the same, but I just haven't spoken to them yet to confirm.

I will definitely take a look at that site.