The biggest thing I'm seeing actually isn't his residency status, but I think you'll have the biggest issue with the value of the properties you are looking at.

But what you’re encouraging is that when I am 23, I should use the first 4 or so years just building a portfolio of LTR’s and then when I am 27, look into leveraging STR’s to meet the “Real Estate Professional Status” and “Material Participation” the IRS outlines, correct? 

In over-saturated areas like Scottsdale, hosts are often asked by guests to discount their nightly rates (especially for extended stays) and many hosts accept the discounted rates because they know that if they deny the request, the guest will simply book with a different host that will extend a discount.  

That said, it can be a fantastic MTR market (if you know what you're looking for and have the network to find the guests).But moreover, why would anyone need a list of 100 cities?!?

These areas won't give you cash flow without significant downpayment, but their price/rent ratios are much more friendly compared to other cities in the Bay Area and you can also benefit from their appreciation.Another thing to put on your radar is the Real Estate Professional Status (REPS) election.

.- Realtor's Oversight: Your realtor may have failed to verify the status of the POS report early in the process, leading to last-minute revelations.Steps to TakeTo address the current situation and prevent similar issues in the future, consider the following steps:1.

Fix n flips are typically dealer status income not capital gain.  

I'm on Airbnb, Vrbo, and Houfy, which is like direct booking - no fee to the guest, and a small yearly fee to the host to list.

This all depends on your tax bracket, state, marital status, etc.

These places are gold mines!