Since they are responsible for maintaining the relationship with you after the transaction closes, this approach adds an extra layer of confidence and security to your investment.

A house hack could definitely be a good first step, allowing you to build wealth while maintaining your lifestyle.

It's important to follow your state’s tenant/landlord laws and maintain a record of any essential notices given.

This way, they’ll have a vested interest in maintaining high standards of management.To truly understand property dynamics and support the management team, I recommend spending time on-site.

My definitions of the classes are (someone else might have different opinion):Class A - higher property prices, low crime, highly rated schools, tenants and homeowner usually higher income (although if the owner bought years ago they could be lower income), streets are well kept, yards maintained, no run down cars parked in street. 

Since your properties have significant equity and low interest rates, you could consider refinancing just enough to maintain strong cash flow.House Hacking:Consider purchasing a duplex, triplex, or fourplex in San Diego.

Theyre expensive, but you wont lose your home to foreclosure unless you move out, stop paying taxes/insurance, or fail to maintain it. 

Section 8 provides consistent pay and the tenants have to uphold the standard put forth by SECTION 8 to maintain their voucher. 

That is something I would for sure have to look into as, according to your post, it seems like the timeline for mid-term rentals kind of lines up with the amount of time that we would be gone each year, which would work out well and probably require less of a hassle of trying to maintain the property after each stay for Air BnB.

If your parents do not have experience and you are eager to learn, you should come up with a strategy with your parents so that you can start managing the existing portfolio and finding a way to grow it.First and foremost I would maximize the property as much as possible now.How well is it maintained - any deferred maintenance?