I’ve come here for some guidance and some advice from more seasoned investors. Any info or insight would be appreciated. Thank you in advance ! I find myself at a crossroads where I need to decide whether it is wiser investment wise to A. Sell my multifamily and with that money put down 200k on a 500k, 500 sq ft condo in Boston. OrB. Invest in another multi family an hour away from where I live, generate more monthly cash flow and rent for $2k in Boston. The market right now in Massachusetts is outrageous and probably at the top of the bubble. I’ve been trying to wait it out but I am getting real antsy.I’m interested in hearing about your thoughts or insights on which investment would be best.Thank you!!

Sounds like you're house-hacking right now in a multi and probably sick of living with other people? This is a fairly common after spending some years there. I really dont think you have to chose. In this theoretical situation, you can use the money from the proceeds of your home (assuming youve owner occupied for some time and have some tax exemptions), purchase a condo for 10% down conventional - no PMI (those loans exist), and put other funds towards a cash flowing property in a secondary market to increase cash flow on a home. Your $150k left from that would allow you to buy a 3 family in the outskirts with great cash on cash returns of 8-12%. Win-win!For those who dont fully understand the appreciation value of the Boston market they might think that a condo purchase is absolutely foolish but given the fact that it'll give you quality of life, tax haven for a lot of expenses, as well as long term appreciation, it's not an unwise decision to be able to get into. Hope that gives you some local perspective :)

From a pure investment standpoint - Multifamily!! Condos come with condo associations, which can be difficult to deal with if you're an investor. Condo values are also the fastest to fall and the last to rise when entering and leaving a recession, respectively. If you're going to owner occupy the condo, then I'd probably go condo. Rents are sky-high in Boston and you'll at least build equity, gain appreciation over the long run, and get a capital gain tax exemption when you sell (as long as you meet the conditions). The upside may be worth the potential headaches.

Thank you all for your thoughtful feedback! There's a lot for me to consider and appreciate the time you all took to answer me.

@Debora Monteiro is it possible that the cash flow from the multi-family is enough to cover the rent? If so, then that seems like a no-brainer. You benefit from having the cash flow and equity build up of the multi-family and have no risk with the condo in Boston, with basically no money out of pocket each month. It’s almost like house hacking, sort of.

@Debora Monteiro generally people are leaving the inner city to avoid other people. Many are relocating to suburbs for some green space and escape from crowded elevators etc. Lots of those will continue to work from home. That would suggest a 500k 500 sq ft condo is not a great investment. I would stick with duplexes and triplexes especially if they are in the suburbs. All the best!