During our relationship, he has purchased a primary home, a duplex for his sibling, several other multifamily for his personal investment.

Having a positive rapport with a lender can help you achieve your long-term real estate objectives.To optimize your assets, think about using partnerships or personal funds.Owner Occupying a Multifamily Home:Owner-occupying a multifamily property in San Diego can be a strategic move, especially with the goal of expanding your portfolio.Understand the regulations and requirements for owner-occupancy in your target area.

A person successful enough to have purchased multiple homes is not going to be impressed by your degree.

Persons over 65 account for ~14.3% of the population.

Know how long it will take you to get title insurance for a resale.Also understand how you will have to pay.....typically cash the same day where I am....at some sales it is cash at the very end of the bidding on that one property....sometimes cashiers checks, every so often personal check, so chances there is no chance for financing. 

@Noyessie Hubert  Personally, I don't think there's any money to be made in this deal but let me know if I'm missing anything.Looking at your numbers:- Best case scenario, $150k purchase, $30k rehab, $180k value. 

I'm trying to decide if the home that we lived in as a personal residence and then converted to a rental is still a good investment or not.

The reason is since I am the owner of the LLC, it's income is reported in my personal taxes. 

I'd go in person and talk to a detective and see what they recommend you do.

When the right person figures it out please let me know.