less expensive markets now or keep waiting in more expensive ones

[Ben Gibson]

I am wanting to purchase a SFH to use as a STVR in the San Diego area and then expand to purchasing other STVRs and LTRs in other less expensive markets. I'm starting in San Diego area at the advice of several other investors who recommended "first purchasing in the market you want to chase the least", meaning that assuming that prices will continue to rise in most markets, even with a correction, it will just be that much more expensive to wait to purchase in the more expensive markets than it would be elsewhere, so we should try to get that one locked in now and then we can move on to different markets.

Obviously, the more expensive markets (Especially San Diego county) are much more competitive so it's taking a while to purchase a property despite having plenty of cash on hand and lender pre-approval. Though, I can't help but feel anxious about having so much cash just sitting idle, especially with rising inflation. 

My primary goal (for several reasons, financially and otherwise) is to acquire a property in San Diego county. I'm wondering if we should continue on the path of trying to secure a home in the more expensive market despite the risk of idle cash OR if it's more advantageous to just start acquiring other properties in less expensive markets now instead? Is there a way to leverage those other properties in order to make it easier to acquire a home in the more expensive market later even if prices increase from where they are now?