Rent vs. Buy in Boston Area

[Emma Ferraro]

Hey everybody!  I'm curious about the thoughts of more experienced RE individuals on renting vs. purchasing in the Boston area. For background, I am a CPA living in Somerville and I'm not new to personal finance topics but quite new to real estate. 

Obviously RE prices in this area are high. Even with no experience, I can see that a house-hacking situation would be unlikely here. I'm renting now and have been for ~3 years since graduating college. Right now I have a pretty favorable rent ($950/mo) living with roommates, but looking to have my own spot in the next year or so and debating the "should I buy a condo or keep renting" debacle. Based on my browsing, a 1 bed rental in Somerville/Cambridge is $1,800-$2,000+ per month, while my mortgage would be roughly $2,500 per month for a <400k property. My main goal is saving as much money as possible and actively investing (which I am already doing). My main questions are:

- Is buying really a better choice? Or would I be better saving the extra $500+ (factoring in repairs/maintenance, etc) and putting it into my index funds

- Are there any areas around Boston where a 300-400k condo is actually likely to appreciate in value in the future?

- Does anybody have experience purchasing a 1-2br apartment, living in it for a while and then renting it out (rather than selling?) Seems like rent prices for a 1br are less than my mortgage would be.

I know these are vague and subjective - just looking to get some opinions as I get started thinking about this!