As a PM I will tell you that Zillow, et all, has made the job of the leasing agent very time consuming.  

Leave my day job?

I also occasionally have random people come to my house trying to intimidate me into paying them to do odd jobs. 

Good job!

I might as well have printed it out and used a crayon but it does the job for non-locals.Green = OK to apply for STR with the City of OrlandoGrey = Within the city but not approved for STR.Everything else = Few if any limits.

I already have an amazing group of guys from my job that not only do expert painting work but can do carpentry, sheetrock, and a lot more.

Be it our job is tearing our family apart or we get medically separated. 

Although I will be retiring from my "real" job in 10 years, this doesn't necessarily mean I will get out of REI at that time. 

depending on the job search) until we move to the Twin Cities.

My new job once I start will start up my savings once again.Basically the decision I’m fighting with in my head is 2 paths to buy my new house and keep my current:1- save up as much as I can from new job.