New to RE Investing from Quincy, MA

[Account Closed]

Hey everyone my name is Justin. I'm from Quincy, MA.  First, I just want to say that I have enjoyed reading the site over the past week, it's been a great learning experience. My background in real estate is fairly limited. I joined a real estate law firm in July of 2015 and have been working there ever since. So, while i'm well versed in closings, purchase and sale negotiation/drafting and title work i'm not nearly as well educated in what underlying numbers make a deal work from an investment perspective. Although I have since learned a bit about the 2% rule and 50% rule.  

In terms of goals, I don't think that I want to have a big portfolio (although this may change the more I learn). What I always envisioned was turning my current condo into a rental after living there for about 5-8 years (it's in a nice location about a five minute walk to the red line, for those non Bostonians that's one of the train lines that takes you into Boston). When that unit gets paid off I would then buy another and so on and so on. My underlying logic behind this is that I don't want to over extend myself. By adding one unit at a time where my salary can cover the rental mortgage and my personal mortgage I view it as a less risky play. 

Although, I have a feeling that it may be the exact opposite, by keeping only one unit there is far greater risk because you could have a situation where your rental portfolio is 100% unoccupied/or worse you're stuck with a bad tenant. This is a very different model from what appears to be the norm of adding lots of units quickly/rehab/cash out refi, etc. so any comments on why my strategy would be a bad long term strategy would of course be much appreciated.  Thanks and glad to be a part of the community!