What Would You Do In My Position?

[Cosmo Iannopollo]

Calling on the collective brain power of the BP community. As you have all shamed me through your ability to act and your knowledge to bring deals together, I come to you hat in hand, a frustrated yet anxious man. 

My wife and I recently moved from CT to MA for my work, and we're currently a single-income house (well, apartment) hold, as my wife is now staying home to care for our new baby. I see you all putting together so many deals, so I figure why not put my life out there to see how you would all move the chess pieces. 

My Goal: Purchase a primary residence and a second investment property. 

What's Holding Me Back: Lack of savings, knowledge and a thinning hair line, but mostly the first two.

Tools at My Disposal: 

• 2-unit house purchased with an FHA loan;
  • Purchase price of $200K (30-year fixed @ 3.25%) 
  • $181K remaining
  • $1600/mo mortgage payment with $2400 in rental income 
  • Area has appreciated with unreliable Zillow estimates assuming a $230K sales price
• $87,500/yr salary (take home of approximately $5K/mo)
• Approx. $20K savings (a reserve I'm loathe to touch)
• 800+ credit score
• Very low monthly debt

Right now, my rent in this part of MA is $2100. My soul dies a little bit each month and I'm not sure I can take another year of renting. 

What I'm Currently Looking At:

• Primary residence for less than $350K
• Lakeside cottage in Upstate NY for $120K to be used as a short-term/vacation rental

So, with all of this, what would you fine people do in my position? Bonus points if you live near Boston and want to make yourself feel great by watching me bungle my way through this all in person.