The same for flips, the learning curve is steep and a simple mistake can set you back or take you out of the game altogether.

You can do something simple like transform a garage or unfinished basement into a "wellness center" for about $10K and then make business connections with local yogis, wellness practitioners, hold meditation retreats and specialized events.

I think applying your existing skills and experience is some times one of the easier ways to get involved in the Chicago real estate game!

For years my prop mgt s-corp has been paid to manage and do work on rentals I own personally or my larger apts I hold in LLCs.  

Hi Sammy,Glad to see you taking steps in your real estate investing career, it helps to get reps in and learn.As for what you should do, your title states that you have "little equity", does that mean there is little equity in the Florida property or you have little available for another equity investment.I'd caution a refi with little equity, as stability in the early stages of your investment career is crucial to long-term success, try not to over extend yourself and potentially end up behind.Having access to investors and partners is the name of the game for scaling and limited funds, if you have access to investor capital, working with a wholesaler to acquire a flip may be a good option just be mindful of the risks of as-is properties and having investor capital at risk. 

I'd make sure the agent you're working with knows the campus and STR game.

This is a great strategy to use your HELOC for rehab and holding costs.

This was my starting point to really get into the game and not only see how things work first hand, but it also inspired me to keep going.

In my opinion the best idea is LTR, self management, and playing the long game.

Although I am doing ground-up for the first time, I have a lot of experience in county buying and holding for long-term asset building and cash flow.