Westminster has been expanding the industrial/commercial areas near the Carroll County Regional Airport and along Route 140 to bring in more of those types of employment and there is a push within the City to revitalize the Main Street area with small local shops and eateries.   

For a rental I'd go the quarter round route.

I understand that this is costly and could go the LLC LLP route, but the cost of the legal work will be spread out over many deals, as well as larger deals. 

Malden and Everett are great choices--Malden has the T stop, and though Everett doesn't, it has bus routes and a strong rental market.

With this scenario, I feel 50/50 is the fair and smart route. 

Househacking with a FHA loan is the route I would possibly take on the next one!  

I often tell clients that they have to think about the end at the beginning...it is not a popular topic and people (understandably) do not want to imagine an exciting opportunity getting sideways, but as @Jessica Zolotorofe mentions, doing it right now is the most cost effective route.  

For years I thought I wouldn't go the MFH route, but after being on this site, listening to podcasts, and reading a number of books I'm more comfortable and see the potential with including those types of properties in my portfolio.Thanks for your feedback!

If so would you recommend it or should I take a different route???

If you're really skilled at door-to-door soft selling to all kinds of defensive people, then this might be a good route, but in general I wouldn't suggest this strategy for NYC.