It's quite literally on the border of Fairfax and Mariemont just off Wooster pike. 

Now that I am on the investor side of the equation I want to make sure that I am foreseeing any obstacles that may come down the pike.

I like the Columbia Pike corridor in Arlington, reasonable prices, strong rents, in the long long term likely a streetcar/metro line/hyperloop will probably be added.

Being at the base of Pikes Peak offers a constant beautiful view.

Im right up the road from you on Rockville Pike.

It's right off the 155 & Gallatin Pike, super convenient location!

Mass Housing's appraisal process is a lot easier too.If you can stay south of the Mass Pike and out of the Worcester hills, you'll have less snow in the winter. 

Anywhere in Pike or Monroe county is a good place to start.

The places I'd recommend looking are Brockton, Taunton, Middleboro, Plymouth, Fall River and New Bedford - the latter two being south coast, not south shore.For example, average 3-plex sale price over the last 6 months:New Bedford: $208.3KFall River: $231.2KTaunton: $321.2KMiddleboro: $382.6KBrockton: $444.3KBoston: $974.6K.Not only do you get more for your money on the south shore, but as you get north of the MA Pike and west of 495, you're into the Worcester hills - about 1,000 feet in altitude. 

That'll be Pike & Warren township schools (north or south of 38th St) which are not the best but good.