I currently live rent free with my father and have about 20k saved up.

After getting my first house (live+rent) approved I'm leaving one of those job.

Find out if those seven tenants have stopped paying their rent, using Covid and the government's Eviction Moratoriums, to live rent-free at Landlord's expense.

Are you trying to get positive cashflow while living it, break even and live rent free, negative cashflow but get a rental?

My desire is to live "rent free", or at least, pay far less monthly than I am paying now (I was paying about $600-$700s for years until my roommate recently moved out due to COVID).

If you have some money to work with, even though the market is competitive you can find something that is a great investment and can supplement your income, allow you to live "Rent free", and sooner or later cash flow.

We have many transplants here, they are very active in local affairs and work to implement the same policies that they are running away from... blows my mind. 

@Owen Schwaegerle I grew up in SLO, and my parents still liver there. 

My wife and I own and self-manage one rental property (first home lived in, then turned rental - and this has become our strategy....buy-live-rent out).

I always tell transplants to rent here first to get the lay of the land.