I am living on the SE side which is ultra-competitive currently.

I am not sure I buy that Pilsen is the one southside of Chicago neighborhood driving rent increases, but it is surely a gentrifying area and factor.I think Bronzevilles & Woodlawn's ability to have more new developments has allowed that entire se coordinator to become a huge factor on the southside.Regardless, whatever you are doing is working so keep doing it!

I have a duplex in SE CC, on a 2.99% 30 year mortgage.

Preferably a local bank or credit union in the SE FL area that is friendly to real estate investors.

We actively invest in TX, FL and 12 other midwest & SE markets that have excellent cash flow and appreciation. 

The property won't cashflow per se, but your housing expense will decrease while your equity in the property grows thanks to principal paydown and appreciation.

I have a duplex on SE Cape Coral….

For primary residence #3, we bought in the path of progress; so, not a live in flip per se but similar in that we will get high organic appreciation and also add value through easy rehab such as refinishing floors and railings, replacing fixtures, improving landscaping, upgrading tile, etc.

It doesn't ban wholesaling per se.

LLC may expose you to SE tax, but only if your income is subject to se tax...