They also have a home vacancy tax in a lot of areas which applies to short term rentals. 

I’m also open to exploring short-term rentals, private lending, or passive investing in funds—anything that maximizes returns while keeping risk and time commitments manageable.For context, I’d consider leaving my job if this could become a full-time venture that surpasses my current compensation (low-mid six figures).

Hard money loans can be an option, but they often come with high-interest rates and short repayment terms.

Bought it as a safe bet thinking it would do roughly $35k annually in short term rents.

Find out what financial problem you are trying to solve in the short term until your able to get to more "long term" problems that real estate helps with 

The one that's short term and don't cost me a lot to initiate/originate.

In the short term, it will be more painful though.Personally, I'm not a fan of enabling bad tenant behavior and in life you get what you tolerate.

Using these parts of local zoning can lead to potential deals.  

Hi Jessica, I would suggest getting a propstream or any other lead generation account, finding cash buyers who bought similiar properties to yours in the last 3-6 months in the area of the properties you are looking to sell, skip trace then cold call or cold texting the list. 

Q2 is most important: If the mortgaage is upside down, it would have to be an approved short sale and that could take a very long time to rectify.