You can attract some of those same tenants in outlying areas as well (think Nike/Intel)...biggest hurdles are future of landlord tenant law in Portland.

One of my biggest hold backs from early retirement is healthcare/insurance costs.

I suspect many of us are going to realize later down that line that it will be cheaper to just forgive these debts as an incentive for the tenant to leave. 

My biggest interest is that I'm able to sell after 10 years and take advantage of the appreciate exclusion.

Biggest question I'd ask is whether or not I could afford the additional payment without relying on income from the investment property.When looking at a potential investment property, look at best case, most likely, and worst case scenarios and decide what the probability of loss is. 

@Steven Arterbery what has been your biggest bottleneck to keep you from knocking on 40 doors a day?

Make some offers and get in the game.No substitute for practical real life experience.My final comment if you want to buy and hold and are investing for the long term.The biggest factor in a successful investment will NOT be what property you buy.

All of this came from a single phone call about someone wanting to rent a home in Denton.Total out of pocket: $0Total net proceeds of all sales related to deal: $120,000My biggest take away from all of this is that it is all about the relationships you build.

I was also looking at Attleboro (great school systems, people willpay a premium for that) and Taunton but Fall River and New Bedford seemed to be the best priced market and the ones that had the biggest chance at going up in value due to the train.

My biggest pieces of advice that I could give you is to start investing yourself.