Ultimately, it boils down to who you know.

My stay at the current place is nearing its end and I'm unsure if it's smarter to buy another primary residence and house hack or just buy another rental with the cash I have saved up and find something else to rent. 

Ultimately, a better W-2 will get you the best bargaining position for future deals, so that is what you ought to focus on.

So # 3 got the spot and mr board member was back on the waiting list as  #1, then I was ultimately bumped back to 3rd.

Hi everybody.Maybe I'm a dummy but could you explain the Financing thing to me.Let's say I save $10k.

I would keep the property and keep my prop 13 protected property tax saving and leverage its equity for the necessary improvements as a minimum. 

You'd be saving the $1300 a month in CC debt, and think about the higher interest rate you'd be paying on the a new mortgage because of your lower credit score. 

Also in terms of insurance claims do people have to wait for the claim(s) to be paid o before you purchase/acquire the property (land/lot)I am talking about a strategy I want to use in CA and I want to save money and have a lot of time I can exchange to get/acquire land potentially 

THe whole point is not to have to live in it for 2 years to save on the taxes. 

@Gustavo GonzalezFor those who are able to save more than $30k a year or have substantial liquidity (over 200k), being a landlord and especially flipping is a lot of work.