You totally rang a bell and I’ll have to certainly go back and investigate.  

Thanks to my high W2 income and not having any debt, it would also be easy to get approved for some cheap 2.x% financing.Having never owned real estate, a good way to get started would be by owning my primary residence for a while, with the intent of eventually renting it out in a few years and in the meantime seeing how I feel about maintenance and home ownership in general.Unfortunately, the areas I am looking at are in very high demand (River North, West Loop, Fulton Market), and have prices such that I would at best barely break even with rent after taking into account HOA and taxes ($300k-500k range for 1-2 bd, HOA in the ~$500/mo).I understand condos in downtown are generally a bad investment, but I really don’t want my quality of life to suffer by moving far just for the sake of home ownership.

As an investment property you can go up to 85 LTV on a portfolio loan with interest rates in the 3.25% - 3.50% range.

Your legal remedy is to force the seller to close through specific performance, and if you had sufficient language in your liquidated damages and default language the seller may also have to pay your legal fees.

Are there a wide range of renters there (Class A?

Self sufficient country people is who I rent to 

Join a MastermindYou have a partner but widen your range of support together.

If you can get one of the tenants to leave before closing, you may be able to do FHA (3.5% down), but for a triplex you will run into the self-sufficiency rule. 

As for the humane part of this, I think 30 is the minimum and 60 should be sufficient for this time of year.

My price range used to be $40-60k for a 3 bedroom 1 bath prior to Covid but I don't know if that is possible given the competiveness of the current market.