Looking for Advice: Single Guy Loaded with Equity

[Jason Clark]

Hi Everybody, 

I'm looking for some ideas/advice and wondering "what would you do" if you were in my position. This is for fun but I'm seriously looking at hitting the reset button for the next chapter of my life and I'm suffering analysis paralysis. I have too many options, to much equity, and not enough education or experience to feel comfortable making a decision. I'm hoping to bounce some ideas around to kick me out of this funk I'm in.

This is probably the third or forth time I've written this post over the past few months and I always delete it since I can't seem to word it in way that makes sense. I'm just going to blurt it all out and clarify any holes if there are any replies.

1. I'm a single guy, 41 years old, no wife no kids, I work in IT in the SF Bay Area but after 17 years I'm tired of it. I bought a rental SFR a few years ago that nets me $1400/mo. I paid 175 cash and it's worth about 230 now.

2. My primary residence has about 600k in equity so if I sell, which I'm considering, then I'm primed to take a big hit in cap gains taxes and fees and who knows what else that will eat up any buying power that I have.

3. I'm pretty much also tired of living in CA and would like to relocate out of state. I'm looking to move somewhere I can buy a couple of houses as rentals and something small for myself. I would then start the process of starting my own property management company as a new career.

My thinking is if I could have 2-3 rentals of my own (paid cash) and ~25 rental units to manage that over time of building the business I could live a pretty good comfortable life. I'm not trying to get rich I just want to enjoy life, ride my Harley, and go fishing every once in a while.

Areas I have looked at are Texas, Montana, and Tennessee (I really have my eye on Knoxville, not sure why). How cool would it be to work on a Business degree at UT while building my own PM business on the side and living on my rental income? It has my attention.

OK I'll shut up now. What do you think, am I crazy? If you had the chance to be in my shoes how would you approach your next move?

P.S. thanks in advance for any advice!

JC