It’ll be tough but I know I’ll push through!

My mother isn't either and her and my dad have a very tough time communicating with each other.

Based on those it does seem like it's going to be tough to even get to 50% coverage of the mortgage in the areas I want.

Your goal #2 is going to be tough in this environment.  

Even 2-3 years back, the prices of triple deckers in Eastie were 30-50% less.In terms of what you should do.. it's a tough decision and completely up to you. 

Would love for someone with more experience to prove me wrong here.

Making the purchase all cash, is not as awesome as it seems – we tied up $195,000, which made things a little tough specially because we finalized another purchase right after this one.Things we learned: (1) having cash on hand is useful, we saved ourselves some money by financing the project ourselves.

It's a tough one that I'm thinking about too.

., with a hard money loan added to what you have, this would be possible, otherwise...NY tough.

Since the markets are so tough right now you may want to consider stacking your capital first.