Starting My Real Estate Journey!

[Michael Saucier]

Hello, everybody!  Long time reader, first time poster.  I'm looking for some advice on where to begin my real estate investment journey.

I am 31 years old, married and have a young child.  We also bought our first home last October in the Greater Boston area.  I am a small business owner and am looking to diversify into real estate.  I've spent the last seven years investing heavily back in to my company and it has grown, and continues to grow, at a quick, but manageable pace.  I've reached the point where I am making a nice living and have some extra cash that I'd like to invest outside of the business (while still investing in the business).

With all of that being said, I'd like to make my first jump in to real estate, but just can't decide how/where/when. Ultimately, I think I'd like to grow my business for a few more years, sell it, and focus on building a real estate portfolio. Or, possibly, continue growing my business and just invest in real estate simultaneously. I am very interested in MHP's; however, I think I want to start out with a condo or SFH - just to get my feet wet and get some hand on experience. I had a few questions for everyone:

1) Obviously, it depends on the type of deals you find, but can you truly find enough good investments where you can comfortably live off the cash flow?  Being in the Greater Boston area, that sounds like a pipe dream.  Prices are sky high and it seems like buying at these levels would not produce much extra cash flow.

2) How difficult is it to invest out of state?  I've been looking at areas with lower costs of living, among other factors.  Obviously, I'd need to hire a property manager if I went this route, but I'm curious to hear the challenges, or benefits, that come with long distance investments.

3) Is "retiring" and living off your rental portfolio a realistic goal?  I'm OK with not "fully" retiring.  I like to stay busy and I love working for myself.  I can envision myself being semi-retired (when the time comes) and still managing/running a portfolio of properties.  Have any of you gone this route?  Any insights to this strategy would be insightful.

Thanks in advance!