Their insurance has asked me to return the month's payment for the remaining days of their rental (Unfortunately, I did not have a cancellation agreement).I am unsure how to handle this situation, especially since I couldn't fill the majority of the rental dates and had to offer discounts for the days I did manage to book.

But yes, I always make sure I walk the property first.

This is limiting my options.I have never utilized the multifamily lending products offered by Fannie, Freddie, etc., so I would be interested to a) hear other BP members' lender recommendations for this sized property and also b) other members' experiences working with Fannie, Freddie, etc.  

Offer discounts for applying in a short time period or- offer a free application fee. 

Ironically, I was ready to let go of multifamily and focus on more lease options, but then my team finally got an offer accepted on a 54 unit.

My team offers turn-key properties to investors like yourself and assists with helping get funded on the back end.

I think that a part time investor can have success with syndicated offerings and triple net leased properties if they’re willing to learn real estate fundamentals, perform “due diligence” on the deal/sponsors/property and engage legal help.  

Unfortunately, NY does not offer many local STR companies due to the regulations that make STR hosting difficult. 

I'm more focused on residential properties, however, I offer a bit of everything.

@Jose Saladin Purchasing your sister’s home as a live-in rental offers instant equity (~$170K), tax benefits, and landlord experience, making it a solid first step into real estate investing.