Commuting isn't ideal but if you can "get on base" with a property/househack a bit outside of the city you can potentially cashflow a bit more, and benefit from an appreciating market that isn't quite as HCOL as a mecca like Boston.My brokerage specializes in multi family investments and househacks in particular around central MA.

But I also realize many people choose the direction of Appreciation first.In my hometown market (not Pittsburgh, but central NJ area), few small to mid size multi family properties could come close to cash flowing positively.

Hey James, I'm sure you've found a solution by now considering this post is 2 years old, but for future reference here is what I have found as far as software solutions for managing a handful of rehab projects at once.Construction/Rehabbing Specific PM Software vs Generic PM SoftwaresWhen choosing your software solutions you will need to decide if you prefer a house flipping software that is specifically built for managing a house flipping business or use a generic project management software.  

Conversely, the number of small-multi family properties being built is a tiny tiny fraction of the number built from the 1950s-1980s in cities like Phoenix and Mesa.

What factors should I prioritize when choosing the best approach for my future success in real estate? 

Or in your case, maybe even change classes of property and use what's known as a consolidation exchange to combine the sales into a larger asset like a multi-family or commercial property.

This doesn't mean that you can't purchase a multi-unit (duplex, triplex, etc.), but I do not believe that you will qualify for VA loan entitlement if you purchased a property that is not your primary residence.

I plan to start my investing journey with an owner occupied multi-family in Albany or the surrounding cities.

Just curious... what’s your ultimate goal for that office space..are you looking to boost resale value, or is it more about having a functional retreat above the garage?

Can we all agree a dollar made in Austin TX or Bryan TX or Dallas TX or San Francisco CA, or Nashville TN or any where spends the same wherever you choose to spend that dollar.