If you have some experience with buying and selling, for me, the best way to go is with a Flat fee agent that will put the house in the MLS and give it the exposure that any agent will give. 

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

Then, roll the excess into rentals.I like your plan for keeping your exit strategy flexible for each acquisition.

But, they will owe you that money whether regardless if whether they buy a property or not.It is when you tie your compensation to the actual closing of a real estate transaction, whether flat fee or percentage based, that would create trouble for you regarding licensure.

Any excess is carried fwd as an NOL.

In Florida right now, market rents have mostly stayed flat for 1-2 years, and expenses and insurance have gone up.

The building stock is like all the other Chicago urban core burbs, so expect lots of 1950's and 60's construction with galvanized pipes, flat roofs, boilers and outdated electrical.

I would start with a duplex that you live in, three-flat at the most.

Most of the time you're talking about land that doesn't have all that much value and any appraiser that's not crooked is going to recognize the land for what it is - you can't comp 15 acres of swamp or rocky cliffs with 15 acres of flat farmland and get away with that honestly, unless the entire point is to defraud the IRS. 

The thread went off the rails when someone suggested subsidies of of compassion for idiots confronting known risks with no protection on their own.So excessive rain is a known risk of hurricanes.