But we could work out a deal where she manages the property, I cover all maintenance costs, and receive the income from the second unit for a specified amount of time or indefinitely.

My mortgage will be roughly $1500/mo and at the current well below market rents I will not cover the mortgage, so they must be raised I am confident I could ask $1k/mo per unit or add an additional $70/week to the current rents, But i also want to try to find a way to remove the storage and garage bays from the tenants so I can rent them out and make additional income.

You are covered.

If you are thinking it's the money...Note that the hard money lending industry has that covered. 

However with 2 units being rented I am able to almost cover my costs. 

Of course there are some good podcasts that cover real estate, finance and economics that you find helpful.  

Many look like they were a quick stand up with whatever Rooms-to-Go had to offer that day, and were just sitting vacant.Again, I have no local knowledge, but after suffering through a few downturns in various sectors, the Orlando market is something I would personally keep a wary eye on.

Can I raise potential May rent now or should I just cover that on an eviction letter. 

In NC, the easiest way to accomplish what you are looking to accomplish is to have a long enough DD period to cover your ability to vet your concerns.

During this time, the markets have been pretty favorable and probably have covered up mistakes that would eliminate (or created negative) returns in a down or flat market.Really depends on the investor.