In addition to STR'ing the main house, he is building 2 more units (ADUs) on the back side of the property.

There are many articles and podcasts from BP that they talk about that.The main thing is fill you up with as many information as possible.

City water with one main at the street and how will they bill. 

I would probably market it more for events, but use VRBO for that purpose.   

The property will be strictly for investment purposes, not a primary residence.I’ve been looking into two potential financing options:Hard Money Lenders (HML) – I’m drawn to this option for its speed in closing, but I know the rates can be higher.DSCR Loans – This seems like a great option for long-term rentals, but I’m unsure if it’s the right fit for my auction property since it might need some rehabbing.I’m also considering purchasing through a land trust or an LLC to add a layer of protection and privacy.So, my questions are:What’s the best way to approach financing for auction properties?

Yes Joel, That would be a business purpose DSCR loan.

I am looking to purchase real estate for both investment purpose as well as to offset as much tax liability as possible. 

Brewerytown and East Passyunk could also be worth exploring.Big projects like Bellwether can boost neighborhoods, but they often take time to show results, so don’t count on them as a main factor.

The main thing I see when coming across this is deferred maintenance.

I think the main thing people would point to as a red flag for Ocala is that it is not a large employment center like Orlando, Tampa, and Jacksonville and as a result may be more exposed to a pull back in values when there is a downturn.