Possible life changing opportunity

[Steve Moody]

First off I want to tell you about myself and my situation, then I want to hear some input about what I can do.

I'm 32 years old and have been a corporate slave for about 12 years. It's getting old. I live in Southern California and the weather is great, but the cost of living isn't. I'm married with 2 kids. I own a 3br condo that has a value of about $520k. I owe roughly $290k in mortgage, HELOC, and Credit Cards.

My wife and I want to relocate to the Portland Oregon area. I could find a job there in which I make only slightly less than I do here. I could sell my condo here and take the remaining $200k or so and invest it into a new home. The home values I'm looking at are around $250-280k.

This scenario presents me with some options. Do I sink a lot into a home and have very low mortgage, continue to work and have more monthly net income? Do I put 20% down on a home and invest the rest? Do I rent for 6-12 months while learning the new area, investing the money into a CD while I wait, then buy something after that? Do I say "FU" to the corporate world and put some of my money into investment property?

My biggest obstacles are:
1) Fear and uncertainty (corporate work provides a steady and known income, Health Ins, etc, what if I lose all my money?)

2) Where to make the money work for me the most (Tying up all my money in one investment doesn't sound like a good idea)

3) Knowledge (why I'm here and reading all that I can)

4) Fear and uncertainty (yes it's here again, what if I screw up? It's not just me I'm making these decisions for, my kids have to eat and have health care and eventually go to college! )

5) The market (is this a good time to sell? is it a good time to buy?)

What would YOU do? Should I start out small and buy a flip, or a duplex? Should I go all out and try to buy a bigger rental property? Should I invest money in a home for me and my family, continue to work, and invest the rest in long term plans (retirement, college)

I feel that I have a big opportunity to change my life, I just don't want to change it for the worse.

Steve