This option would require assembling a local team as I'm considering forgoing a property manager.D) Invest in a Better Maryland Area: The goal would be to find a property with higher appreciation potential, though I'm aware that the cash flow might not match what I'm currently achieving.Given the unique circumstances of my current investment—significant appreciation, a specific tenant base, and a low mortgage rate—I'm weighing these options carefully.

I would recommend first establishing what your financing options are based on your cash on hand and cashflow expectations....  5% down? 

It was not an option in our house to rent year round.

Whats available - private money or HML will likely be very pricy.One option could be to look at HELOC options on the investment condo - probably not going to get to the full $100k but could help. 

Before you go looking further into options, do note that using bank financing like a 203k to cover construction costs comes with a lot of extra paperwork.

Initially I was interested in short term rentals but after researching and hearing about restrictions in the area, I believe medium term rental might be a better option (or possibly a combination).

All three houses cashflow and she is not interested in selling at all as this is her retirement plan and main source of income, however due to excess cc debt, a high DTI, low credit score and lack of financing options, she is extremely cash poor. she is at the point where she could and I think should declare bankruptcy on those cc's, and move the houses out of her name. in order to get financing, all houses need to be in LLCs, which they aren't.in order to kill a couple birds with one stone, my mind goes straight to 1.

You have a variety of options on how to begin this thrilling adventure.

Yola, Freehostia, Biz.nf, Tumblr, Blogger.The other option is to sell. 

Interested in learning more about multiplex investing and financing options.