After he was successful in being more profitable than his neighbours (one thing he's done well with is driving traffic to his direct booking sites to cut out the host sites that take so much in fees) he started taking on investors that put the 20% down for say a DSCR loan.

It can be pricy but well worth the money if you can afford it. 

I will carefully consider the information you've provided, and it will undoubtedly assist me in making well-informed decisions moving forward.

As well as nails and screws removal and patching large holes from walls.”

Any other possitive factors  - stable tenant base  - alarm systems  - regular checks on the property  - no pets  - Lead safe certification  - newer roof, plumbing, electric, etc..Anything to balance off the lossesBe prepared that it may end up in a non-standard (surplus lines) market for a couple of years.If you did not have flood coverage before, see if they will continue the current policy if you get Flood coverage and increase the property coverage deductible. 

I have also read that having a sizable emergency fund is vital, as well.

It does also cap rent increases to no more than 8.5% which while annoying (probably most especially in NY, where price of living is high), does at the same time help the tenants out as well as helps stop tenants from leaving for no reason other than huge rent increases. 

There is a a common theme as well and they all come from the same guru who may or may not be mentioned in this post. 

Attention: Beware of Non-Bank Fintech AppsI hope this message finds you well.

Seasoning on the money from the personal loan could be a factor as well.