Security deposits have to be held in an escrow account disclosed to the real estate commission which requires a yearly report and all leases need to disclose your license information.

No one really gets back to you with updates like how Airbnb does... you just wait to see if it gets approved and then they'll deposit into your account. 

However, we just started STR property management and it would be very helpful/look more professional to have the ability to esign contracts, autogenerate payout statements, direct deposit payouts, ect.  

For clarification, Fannie Mae and Freddie Mac aren't lenders, so you won't be dealing directly with them.2. 

Unfortunately, since you are in NYS, you only have 15 days to return the security deposit, and getting a contractor out there for a quote (much less, three), is not going to happen. 

I saw the building has tenant and even upstairs which is direct to roof this one I got in first floor.

I have had a few tenants sign up for these services but with our management software the companies just deposit the funds using their portal.

If there's a clause that allows you to back out due to new findings or due diligence conditions, you might be able to retrieve your earnest money deposit.

Substantial deposits (2- 3 months rent) and thorough vetting are the best ways to mitigate.  

Feel free to reach out directly with any questions.