Through that lens I will try to answer your questions to the best of my ability:1.

The ability to get funding in just a few days can make a world of difference, allowing investors to act quickly and lock in the best opportunities.I’m curious, in your experience, what strategies have you found most effective for building strong relationships with reliable direct lenders?

Never heard of a voucher tenant being responsible for maintenance and repairs, rental licensing fees, lead testing upkeep, cap ex, reserves, book keeping and tax prep......and even if you self manage, it takes up your time and should be treated as an expense because its taking away from your ability to earn income elsewhere. 

I definitely understand everyone else's practical advice regarding "lifestyle investments" but also think there is something to be said about following what lights a fire for you! 

They can go practically anywhere.Emotional Support Animals can be any type of animal - dog, cat, horse, peacock, komodo dragon...

Maybe selling is an idea worth considering if the house is a Mona Lisa and kind of beyond the general reality of typical tenant's maintenance obligation and ability, and they aren't paying for the additional quality.If you really want to keep the home, you may find a way to be very happy about it with the right team, whether it be property management, electricians, contractors, or tenants.

They can fine you for practically anything and they want all the STRs to be banned from the city.

In practice rents will be slightly lower and sometimes slightly lower.

So, I DON'T trust my ability to determine someone's character based on a few minute casual conversation and I DO trust my ability to manage even difficult tenants. 

However, I don't know from a practical point of view if it's doable 2) Condo vs townhouse vs cashflow: I noticed condos  and townhouses are way cheaper in fort myers FL ( however risk of hurricanes) and maybe more opportunity for cash flow.