As another Boston resident, I'm extremely hesitant to purchase because I'm fairly confident current prices aren't sustainable and I want to be there to purchase if prices do go down.
I've kept my eye on real estate prices for the past few years and we definitely hit a plateau around summer 2018. Nowadays I see a lot of properties sit on the market for months - quite the opposite of how this "red hot" market is supposed to behave.
I just don't see the fundamentals supporting current prices. A lot of properties are going for 20-50% more than they were previously sold for (in 2012-2014 usually).
On the other hand, rent has NOT increased by 20-50% in that amount of time, and (in my own experience) rent has been pretty flat for the past year or two, except for a few neighborhoods like Allston that have definitely gone up. If rent in a unit stays flat for a few years it's basically impossible for that home's price to keep going up, and since we didn't pick up amazon HQ2, and have tons of luxury development coming in to absorb any other top earners entering the state, I personally doubt there will be much room for rents to grow.
That said, we're no SF. If you work in tech there's probably properties out there you an afford. It just might not be in Somerville or Cambridge where everyone wants to live. Some suggestions: Decent single family in Wollaston neighborhood of Quincy goes around 600k, and further down towards Quincy Adams theres a whole bunch of options. There are occasionally good deals that pop up walking distance to the T in Malden. West Roxbury has good deals almost always. Roslindale isn't totally gentrified yet so you can always jump on that bandwagon and look for a property near Forest Hills. Condos are pumping out in East Boston too although I haven't checked prices lately they might already be too expensive.