New Investor in Massachusetts

[James LaRocque]

Hello BP! I'm James and I'm currently 29 years old and looking to get my start in Real Estate Investing. I'm successful in my day job, but looking to supplement that income and maybe retire early one day. I've been lurking in the backgrounds of BP reading posts for awhile now, but this is my first post.

I have a couple different ideas that I looking at to start my REI career, would expect mostly buy and hold, which I'll list below.

1. I currently have a condo that is my primary residence in Salem, MA, I've owned this about 5 years now. As the economy has gotten better and my job more stable I've been itching to get back to Southern NH, though I haven't been able to decide how to handle the condo. I know in the current market I stand to make a lot of money by selling or renting. Any help in how to appraise this situation would be great.
2. As I feel my local market is a bit steep for what I feel I can afford, I've been considering looking elsewhere. I've read David Greene's "Long-Distance Real Estate Investing" as well as some posts on here, and have been looking at the Midwest (Ohio or Indiana maybe) and possibly Memphis. Though I really don't know much about these areas.

Any suggestions would be appreciated.

-James