@Justin Goldwater Dude, at first, I thinking: "This guy is totally describing Denver," until I got to your second condition. My immediate next thought was: what about Colorado Springs? Ok, to be honest, that markets is just as competitive and no longer falls in your target price. To be honest, I think you will be hard-pressed to find the city you describe: Fun place to live, healthy economy and increasing job prospects, strong University system, and cheap starter homes. That is what every person is looking for, let alone every investor.
But, I'll do my best. Here are some of my thoughts:
1) Look to the midwest and the NE. I'm thinking the rust belt cities like Columbus, OH or Cincinnati or the colder New England states like Maine and Vermont. Will that fall in your price target? I'll leave that question to the local real estate experts.
2) I do think you're starting with the RIGHT question: Where do I want to live?, especially with the freedom it sounds like you have now. Take advantage of this opportunity, because will always be opportunities to invest, but time is the one true finite resource. In my perspective, that's what this REI journey is all about: How can I live the life I truly want to live?
*Also, BP tip, other uses have certain keywords flagged, like "Burlington," which will draw attention from those local experts. My post will likely draw some attention for you from the places I suggested above, but if you want more specific markets, add those to your post!