Section 8, nice housing!

I am currently house-hacking and will have an empty room.

I am well versed in pretty much every facet of Real Estate: house hack, LTR/MTR/STR, multifamily, and fix and flips primarily.Aside from that I am also (somewhat) a serial entrepreneur, having started and sold multiple business' over the last 15 years.I also meet with 20+ professionals every week, through referral groups, meetups, and just 1 on 1 sessions trying to get to know people and make connections.I would love to chat with you if you are looking to meet people and get more information about real estate in San Diego!

If you are married, put the debt for the family house in only one person's name.

If you walked into a bank, your pre-approval would likely never qualify for a house hack duplex.Did they count 75% of the expected rent towards your DTI? 

I don’t intend to occupy the house as a primary residence but purchase the property as an investment property. 

In addition to STR'ing the main house, he is building 2 more units (ADUs) on the back side of the property.

@Jacob Flaxman, I am not familiar with this market, so take what I have to say as more of a general comment.My first thought is $250k to build a two story, two bed "house" will cost more than $250k. 

I'm interested in investing in multi unit properties and potentially get into house hacking.

As population grows, housing demand increases, driving rents higher.Rapid and Sustained Appreciation: Not all cities with growing populations appreciate rapidly.