If you buy, rather than stay and save, you likely will see a similar about of savings in property appreciation especially if you can do some value add.  

Get insurance quotes on similar houses to what you are looking to buy BEFORE you even put in offers.

Truthfully I'm struggling even finding a solid real estate agent.Can anyone provide advice or similar experience?

I am in a similar situation to you in that I am in a 100% commission sales job and the number of deductions and the whittling away of your effective tax rate is very powerful once you can wrap your head around the numbers and the big picture.

If the end product is similar to conventional construction, and is compliant with applicable building codes then I think you're good to go.I think you should also consider where you might start. 

Then, you'd use the data on Airman or similar services to determine whether the metrics fit with your personal investment/return objectives.

If this past Sep24 and current Oct24 doesn't mirror Sep 2007-Oct 2007, which if you read the news articles back then to now you'll see how similar they are.

I fear Las Vegas will be similar to the size or BP2023 in Orlando.  

Hey, that's a great question and definitely a smart one to ask when you're diving into the details of STR (short-term rental) investments.Let me break this down from both a tax and practical standpoint based on what I’ve seen with clients in similar situations.

Idea is I could “trade-up” houses, get some trapped equity out of condo, and eventually keep this in my portfolio long-term, for a similar PITI.