I have a duplex that I owner occupy here that works great, however finding a new deal that makes sense is difficult in Madison.I grew up in the Janesville area but really am not familiar with it anymore in regards to the neighborhoods.

it is going to be extremely difficult to buy a property in a market you don't know and don't live in, and operate successfullyfor example - don't do thishttps://www.biggerpockets.com/forums/48/topics/1137397-balti...

buying a money pit you haven't seen in a market you don't know thousands of miles away, and then being beholden to agents and contractors and others you've never met.https://www.biggerpockets.com/forums/48/topics/1137397-balti...https://www.biggerpockets.com/forums/48/topics/1160450-run-i...https://www.biggerpockets.com/forums/963/topics/1195280-expe...the market right now is unforgiving and it's going to take something difficult or creative to be successful. 

It sounds like a poor business decision but its very difficult to get cash flow in A class assets.

I am trying to learn the free way since I agree I need whatever money I have for my next investment and I find it difficult to navigate so much content at every angle.

I am finding it extremely difficult to be able to find financing solutions to land the next one.

The small market size and relationship-based transactions make it difficult for new or smaller players to participate, which aligns with the earlier observation about the lack of services for individual investors.Overall, this market seems to present challenges for growth or democratization, as its current structure favors established, well-connected players with significant capital.

Without knowing more about your situation it would be difficult to know the tax ramifications in your particular circumstances.

ADUs can be extremely difficult to structure since they are usually on the same parcel/parcel number.  

If you have a toilet down there already, adding a shower isn't too difficult.