Buy a cheap place now or wait and save?

[Sam Tanner]

Hey y’all,

I am based in central oregon and my fiancé and I are looking at purchasing our first home and begin building a portfolio of rentals. Currently our savings are pretty low, mostly because a significant amount of our cash is in the stock market and below water at the moment. 
 
We have two paths we could take. Option one is to buy a pretty cheap little place (using either an 80-10-10 mortgage/HELOC or 80-20 with some help from family) now while rates are still relatively low and housing prices in the Bend area have seemed to have tapered off a bit. With this option we'd end up with a dinky home that's not immediately in the desirable part of town but close enough to command rent that would close to pay for itself but is less likely to rapidly increase in value over the next few years due to its proximity to the highway.

Option two is to wait and build up savings. I estimate that if we wait 9-12 months we will be in a place where our purchasing power will be more in the 700-800k range. This would allow us to purchase a home (at today's values) in the desirable part of town with either an ADU or an STR permit. Obviously the risk here is rates, inflation, and appreciation.

What would you all do? Would you wait, would you buy something cheaper, or would you figure out a way to finagle something nicer now? Looking for any and all opinions, no matter how out there!