What kind of help did you need?

@Dale Orcutt , If you have rented to portion of the house, (House hacked), the investment portion of the qualifies for a like-kind exchange. 

@Shane Gaboury I don't know what kind of building stock is in your area, but in my opinion, multifamily investing will normally beat condos all day long.

The idea is to own enough rental property to support me when I need the extra help, fund my retirement, keep my parents healthy, and take care of my possible future family.

Most students want to be close enough to walk/bike so the only way you'd be able to lure them away is to have really cheap rent, which wouldnt support the cost to build new.If you do build on the lot, then I think you'd have better luck marketing to the medical workforce. 

The tenants of that property didn't seem to take good care of the property, so that kind of questioned the type of tenants we would attract in the area. 

Family financial dealings of any kind are fraught with danger as one is always walking on egg shells.

I wish I had the kind of tenants who could pay rent "digitally" - but a fair amount of them still deposit cash in the bank...on the 5th.

Also since you are in San Diego, one of the hotter markets, maybe it would help us if you could give a ballpark of what kind of appreciation and ARV value you got and what it cost you to move to the next house.

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