I don't know if you mean this to be an STR or LTR (I am not familiar with Oahu rents but >$3k/unit that close to the beach does not seem outrageous to me), but if an STR, I wouldn't do it at the current time - Hawaii is too likely to suffer from the Covid-induced hangover for air travel that could impact tourism there for months or even years.  

I just commissioned as an officer into Air Force this week and will be at my first assignment in the fall (central Texas).

I started looking into Chicago IL because multi-families are quite popular there and its a pretty hot real estate market.However, this would be my first property.

Unlike costal/hot metro areas, you're not going to get great appreciation but that's also why it's affordable here.

It is smaller, so it needs to be moved around and I circulate the air by leaving the furnace fans run.

Or, as you referenced the quote its basically up in the air and just back to the IRS written rules?

$3250 does seem about 2x what a SFH 3/1 is going to get in Midland: https://odessa.craigslist.org/apa/d/midland-casa-nueva-de-3-recamaras/7135360959.htmlSFH generally don't have owner expenses for any utilities, which is nice.If Midland is a hot rental market then your vacancy should be low. 

If I said I was only accepting rent from healthcare workers, but not lawyers I’d be in just as much legal hot water as if I refused S8, but not the trust fund kid. 

The market we are in is extremely hot for sellers, such that most duplexes have multiple offers at or above asking after only a day or two on the market, which makes it difficult to request additional information ahead of making an offer, such as the lease, yet remain competitive and timely. 

If anyone spends 5 minutes in the area, they can see that they are hot!