First Time Buyer - SF primary residence or house hack?

[Matthew Delcantaro]

Hello BP Community and thank you in advance for any feedback. First-time homebuyer and a first-time poster to BP. I am looking for some guidance on diving into the real estate world. I have a background in FP&A and I'd like to leverage that as well as my interest in real estate (and some savings) into some investments and potentially a career/lifestyle longer term. Here is the dilemma and question to the community. Should we house hack or purchase a SFR (as primary residence) and, assuming we house hack, can we use that equity to leverage the purchase of a SFR?

Some more background and context…

My wife and I (recently married) would love to own a home. We've been renting apartments for the better part of a decade now and know a SFR is the ultimate goal for us as a couple. Additionally, while I know it is impossible to time the market, the market has undoubtedly taken a large swing in favor of sellers (we currently reside in Westchester County, NY). We'd be willing to stretch the commute out, and frankly would need to in order to purchase something we're looking for but will likely need to remain within a 2-hour (1 way) commute of NYC for the foreseeable future.

Alternatively, I’ve discussed the benefits of house hacking with my wife and she has reluctantly agreed to give it a go, but it would need to be on a shorter-term timeframe 1 to 2 years max. I’d then like to rent out the multifamily and leverage, if possible, the equity from that investment property into our SF primary residence.

From what reading I have done it seems the consensus is to not wait for the market to invest, but does this apply to a primary residence as well (what about a potential bubble environment, maybe another post required…)? I understand that the market is cyclical, I am just reluctant to jump in after seeing such large increases in home values over such a short period of time. I personally feel like house hacking would be the way to go especially considering I want to get into REI anyway. At the end of the day this feels like a big decision, and I thought it would be prudent to gain the insight of those that have more experience than myself. What am I missing? What questions should I be asking myself and my wife? What risks are there in both scenarios? What would you do?

As an aside, I am always interested in learning, networking and getting involved. Don’t hesitate to PM me to chat more or connect.

Thank you,

MD