If you have a few reputable buyers, you can search specifically for deals that match their criteria making it much more likely that you'll find a buyer for your deals...Of course, you also need to know what a good deal looks like. 

Eventually I want to be able to (hopefully) own enough properties to rent out and match what I make at work with my rentals.

Then try and match the colors from there with the style of the house. 

Basically, you have to give them your bank statements and they generate an income profile based on the deposits into your bank account. 

The only thing I can think to do is document everything with email notices to her, and possibly begin deducting it out of her security deposit, which I'm not sure if I'm even allowed to do. 

If you have the cash deposit, and you're getting $800/mo positive cash flow, along with depreciation, and expenses to write off, cash flow and appreciation...Fort Lauderdale is a booming area.

He is trying to take me to small court claim to get more of his security deposit back claiming I breached contract by entering the house.

Get a signed lease and security deposit on your current home. 

I targeted this area as many properties match the 1% rule and we're built in the 1900's to 1920's and have fantastic foundations here in Milwaukee.

If you know where and what you want to invest in, contact an agent and ask to get automatic alerts when properties hit the market that match your specifications.