House Hacking In Expensive Markets

[Mike Levene]

Hi all, I recently started an informal real estate group with some old college friends. They are all looking at strategies to use for their first deal and many of us are leaning towards a house hack to reduce the amount of capital we need upfront. The problem many of us run into is being in New England, many of the markets are high cost, high appreciation markets that we either can't get pre qualified for, or even after moving out will struggle to cash flow.

Another big constraint is that many of us have W-2 jobs in engineering that require some days in the office, and these types of higher paying jobs are primarily in major cities (most of us are in the Boston area).

Lastly, a lot of us have significant others that may be less interested in living somewhere "random" because it makes sense as an investment. If they were married, I'd think it would be more of a conversation about their future, but I can understand that if you are only with someone for 1-2 years they might not be willing to pack everything up and follow you on your real estate journey right away.

Any thoughts or ideas to help us sort through the weeds on how to go about finding a house hack with these constraints? Are there any markets outside Boston that any of you have had success with a house hack or tips to succeed in this type of market? I'm sure something similar applies to those who live in high cost cities like NYC, San Francisco, San Diego, Seattle, etc.