So when the day came that I walked out of my b*llshit soul-sucking corporate cubicle job, I had a decision to make; "Retire" for 5  years or invest in myself and my future with the money I had. 

Maybe you can list some of the types of jobs you've done?

I don't want to "Put lipstick on a pig" but I want to do a nice job. 

Are you paying for the job or paying hourly?  

Your fiancée would benefit from looking at getting a w2 job because off the books income is not going to count.

I relocated back to my hometown of Memphis after retiring from my job of 27 years.

The other is once he has the job locked down, he doesn't really have an incentive to fix it fast since there is no real reward at the end of it while you have to cover the carrying costs. 

Good job @Kevin Moules..you said everything I was going to say!

Good job being open to this kind of experience so early.

Go where the job market is strong and will continue to grow.