Regarding the original posters question, I bought my place about 5 years ago at about 30y/o. . .it worked for me, but having a house, especially in an expensive market, ties you down. You can't take a job opportunity in another city as easily, you can't move your stuff to a storage unit and travel for a few months, and you have a lot of net-worth locked up. Additionally, selling has a high transaction cost, in my area I would say 2.5% + realtors at 6% for a total of ~8.5%. That being said, for me, it was a good decision, I bought at the troth in the market, fixed up the place and got a lot of equity while getting a place to live for less than rent.
My house was a gut renovation and I did a lot of renovation myself, but still had to hire contractors to do a lot of things and materials alone are expensive. I had helped on a lot of home improvements growing up, but doing it myself was a learning experience.
I don't rent out rooms on any sort of regular basis as it is a 2bdrm, I work from home, and like some privacy.
I would really ask yourself if you plan on being in that house for a long period of time. It sounds like you have been in your high wage job for ~2 years, do you think you will want to move to another city or another side of the city or need a major break from your job in the near term?
Also, for what it is worth, I would disagree that a buyers agent doesn't cost you anything. . .if I was a seller and was able to not pay the 3% to a buyers agent, I would discount the price. I have no idea what your house will cost, but let's say $300k as I think that is inexpensive in Boston - your buyers agent would cost you $9k which is a lot of negotiation to pay for. . . and a RE attorney would charge a lot less. If you were to use a buyers agent, I would suggest Redfin at least you get a rebate from them on this exorbitant fee.
Oh, there are others that could speak to this with more authority, but if you plan on doing a major renovation and later plan on renting it out - you should keep careful track of your capital account so you can track for capital gains and depreciation later down the road.