However, I am thinking of having my parents who are retired living there part of the year and doing STR for the remainder of the time.

My wife and I just closed on a duplex in Oakland, but the basement/garage was already converted into a separate living space with a bedroom and bathroom.

Even though we live in earthquake country, this was a new experience for us.

Do you want to live there?

Have enough that after you buy the property you still have 6 months of expenses in reserves that you can use for daily living.

A little about me for context: I live in a very expensive market in Rye,NY. 

So they will rent without buying even though buying is available to them but they dont want to live where its affordable.

Live off of equity as you sell or live off cashflow.

You'll likely also reduce your cost of living by moving to a stabilized apartment.Depending on the cashflow and debt paydown, you can use this strategy until you've built enough equity to reinvest.On the other hand, getting into a multi-family after refinancing will also help you build substantial equity to rinse and repeat in the coming years.

I live in jersey but bought my property in Pennsylvania because jersey and NY are extremely expensive.