I admire your drive that you started so early on in life:):) the SDSU neighborhood has some pluses( most important for you as a hacker, renting it around the clock and pay your share and cover the cost, also building long term equity more so with these historical low rates,, also whether SDSU or any other neighborhood in San Diego( which isn’t easy to find properties in that range BTW) is safer with the forecast that they say close to 10m households unfortunately can’t keep up with their mortgages by Mid 2021:(very unfortunate) and being at 400-500k price point it’s just safer for this climate, so lots of time for you to take bigger chances and risks in a more stable environment to achieve you goals.

@Joshua PeglowWe work with a lot of house hackers in Denver and Colorado Springs who are looking for that mother-in-law suite, basement apartment, ADU thing.

If you want to learn how to do something (landlording and light rehab and property ownership as a house hacker), you take a small bite to start (2 french fries), instead of a large bite (4 french fries). 

However, I have not looked at the rules in HR for medium term rentals (30+ days.)We have three properties under contract now for house hackers, none are multis.

We have closed for house hackers all over Northern NJ and with a VA it is a bit harder, but it's less competitive now so there are some opportunities out there.

For instance, a yard may not bring you more income over the long run, but many house hackers also want a white picket fence. 

Can some house hackers provide insight into this?

There are a ton of house hackers on the north side of Chicago.  

I am a relatively new house hacker in a duplex up in northern Colorado. thought its a different price point understanding loans has been the biggest help for me, so I can fully understand what I can buy and what I can not.

Obviously you also want good rates and a loan product that fits your needs (most of our house hackers in Milwaukee use a 5% down conventional portfolio ARM loan with no PMI as opposed to an FHA with PMI for life and which is also not popular with sellers, because of their secondary inspection, especially on 100 year old duplxes..).