Working a 9-5 job with very little return in a 401k and Roth IRA and having to work until I'm dead is not a life I want to lead.

Your job is to determine if the risk is worth it.If you are are just thinking out loud that you may want to sell in 5 years, given your own statements that it is making great cashflow for 5 years, then who cares? 

@Eric SmithI would use 99Designs for higher budget jobs and Fiverr for lower budget items.

We have a great handle of the city, and my day job allows me to travel to all of the smaller communities surrounding it.

Here I am putting down 25% of my money, have a great credit score of 780, have a job showing good income and yet they still want to see all my other financial documents.

I'm looking for someone who does good work at reasonable prices, shows up, and finishes the job. 

This simply isnt the case in the REO world.Also, a listing agent on an REO is acting much more akin to the job of a property manager as opposed to a traditional listing agent. 

My goal is to do so primarily through rentals and occasional flips.

If they balk, they don't get the job because I'm not going to eat their tax bill and I'm not playing patty-cake with the IRS.Keep smilin'Dennis

$2500 in cash reserve is very small to me, you have personal mortgage and student loan to pay, if all goes wrong like lost a job or something, $2500 doesn't last a month.