As for withdrawals from balanced diverse equity/bond investment accounts, Bengen's popular 4% rule with the Monti Carlo math doesn't lie: for nearly everyone, withdrawing 4% annually should allow the nest egg to live out >30yrs under most all 'worse-case' financial climates.

Wondering if you think this is a good deal with the current market climate? 

Start with one unit and move onto the next with the current climate in mind.  

We're seeing example after example of homes with quality rehabs setting the market after fierce bidding wars and sales prices $10k, $15k, $30k above the asking price - maybe they see the current market climate as an opportunity to push.

What's the climate of your current market?

If you’re going to be moving (by the way, I admire your hustle and willingness to move to a different state for your future), pick a place you’re going to want to live in..from what I know Arizona is similar climate and culture to where you’re at; that very much does matter.

I'd start making calls to your repeat buyers and ask what their expectations are in the current climate.

In addition, cities can change their STR rules at the drop of a hat, so you want to make sure you understand the political climate in any area you plan to buy an STR to get a feel for their appetite to regulate STRs.

At the very least I can council you through the current buying climate. 

Looking at the long run, I would also be concerned with the potential impacts of climate change on the ski season.