Boston newbie investor looking for some direction

[Brad M.]

I'm new to BP and thought I would share my situation to see if anyone has any words of advice for a beginner. I own two properties, 1 primary and 1 rental. The rental was my primary until my wife and I needed more space for a baby. We had the means to hold on to it. I’ll preface by saying I want to be a buy-and-hold investor. It’s a numbers game so I’ll cut to the chase…

Age: 30

Location: Boston, MA

Rental: 2 bed, 1 bath condo in South Boston, MA

Purchase Price: $370,000 in 2013

Current Mortgage Balance: $300,000

IR: 3.875%

Type: 30 yr fixed

Rent: $2,600/month

Current Home Value: est. $475,000 (South Boston market exploded after we purchased)

Primary: 3 bed, 3 bath single family in Wilmington, MA

Purchase Price: $535,000 in 2016

Current Mortgage Balance: $420,000

IR: 2.75%

Type: 7 yr/ARM

Available Cash:

$60,000

$40,000 – will be available in August 2017 (Stocks vesting)

With all that said, I'm having trouble figuring out where to go from here. Boston is extremely expensive. Even though my condo's value increased by 25%, it's not cash flowing as well as you would think. Not only is it expensive, but most homes were built over 100 years ago so they can be maintenance money pits. Do I focus on paying the mortgage off on the condo first before getting another property? Do I leverage the equity with a HELOC to get 1 or 2 more properties this year? Or something in between? All I know for sure is I want to be a buy-and-hold investor. My end game is to get to around $20K net/month in rental income and then retire but of course that is subject to change. What's the best way to do that?

Any tips at all would be much appreciated!!!