While short-term rentals in areas like Kissimmee, Florida, can pay for themselves and offer lifestyle benefits, the ROI typically doesn’t match what I see from my traditional portfolio of long-term rentals in North Texas.That said, short-term rentals can still be a great choice, especially if you're drawn to the area and the opportunity to combine personal use with investment income.

I could go on and on, but basically I would love to get any insight into how I should approach this opportunity.  

What's the opportunity cost of letting that equity sit and taking a loss each month?

Many would suggest against RE investing using retirement money but if you go into low risk opportunities it can be a powerful diversification method.

Investing in Wisconsin and Illinois is a great move—both states offer solid opportunities for multifamily and single-family rentals.If you’re looking to connect with like-minded investors or agents, I’d recommend joining local real estate meetups or REIA groups in the areas you’re targeting.

I would keep it in a high interest bank account might as well earn as much gain as you can no matter how small it is.However I think some debt pay down would be great not to the point where you are not liquid enough to Jump at another opportunity or can’t make a major repair when it arise.

The motivation is not necessarily to scale into larger opportunities but rather to achieve better balance and also optimize the performance of the projects and types of projects I currently pursue.I have no shortage of individuals who possess specific skill set who would want exclusive rights to that particular service vertical in return for contributing capital and a partnership interest (construction background and wants to take over all construction duties or someone who is a sales broker and wants to list all of the properties etc.)

You can identify good cash flow opportunities on a fairly large scale. 

An algorithm will probably tell you that undesirable property is an amazing "value add" opportunity. 

Within my 20 years of experience, I've seen West and Central Florida offer great opportunities across different markets.