So it looks like you would need around 4-5 years to get to break even by selling those stocks and paying the tax now. 

You are out in Cali so it is tough to get a good cash flow deal but if you have a comfort level check out states Like Indiana, Ohio, Florida, Las Vegas, Tenn, Georgi and a few others.Unlike Cali you can still find a decent 2-4 unit in states Like IN, OH and FL for under $250K with rents at or above $1250 a door.

This particular home will not likely sell as a flip for more than $50-60k.

The best thing about being a pilot is you will have a captive audience hours per day, with likely at least one of those audience making about $300k/yr. 

I have my 2023 taxes Non W2 and hope to have my 2024 Taxes Non W2 back end of this coming week. 

This is more about inventory and not STR returns. 

At the same time I feel like some of the market rents they are willing to pay are over what is realistic and may be contributing to inflating the broader market.

It sounds like your question is what is the conventional guideline on using these rents to qualify ?

I believe in some states leases over a certain length of time need to be recorded like a deed to be enforced.

I would be happy to connect despite being an out of state investor like you haha