I also bet a good guy name Mark Shaffar recently on BP who has deals in the midwest and Milwaukee.  

Is there a strategy to implement to increase my odds? 

That is very odd, i just closed on my house a few weeks ago in VA.

I bet it is a bigger dream than the "dream job" you moved beyond.

Single-family homes look like my best bet so my investments will probably begin there.

Thank you so much, this is exactly the answer I was looking for, I was hoping for a better answer that would benefit me in finding a good warranty but it seems as if the odds are more against me. thank you for being so open and thorough!!!

Yes, sales prices in the FL market overall have increased recently - but betting on appreciation is a gamble.

I guess my main concerns are these two things 1- the guy who has less experience in the maintenance department is getting paid the same as the guy who got the deal and is keeping the books (me), and as the guy who actually knows how to do the fix it stuff, and 2- I am concerned that when the rubber hits the road and a tenant moves out and the place needs to get painted, recarpeted, and all the other odds and ends to get it rent ready, that these guys what with their full time jobs and what not will not be able to do what is necessary.

it's a trap. i bet she just had a conversation with the coworker and automatically assumes they want it. she wants to get out before even the coworker applies. then it's "your problem"

Hey @John Davis Welcome to Biggerpockets and congrats on your second property, that's a lot of success despite odds.