We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

I had a call with a loan officer yesterday and I am very intrigued, but haven't heard much in recent discussions for this product or found anything in the search bar for this bank. 

I do not wish to waste my time watching videos,searching the internet for how tos and what I should be doing.

I would search for other HML

I would closely monitor your competitions pricing to see what is working for them.Vrbo has built in tools to monitor when people are searching for specific dates.

Also searching on idealista website which is a great one to start with.

You can also check meetup.com or search Facebook for real estate investment groups, clubs, or meetings in your area.You're feeling FOMO because you see people all over BP, YouTube, and Instagram bragging about their success.

From internet search/Turbo Tenant:  'In certain instances, breaking a lease in California due to a medical condition might be possible.

I havent relocated for opportunities but have some experience with Mid-term rentals - For MTR I would find major hospitals and then search the houses around them, if they are priced really high / numbers wouldnt work, eliminate that market.

If you're open to expanding your search some time in the future, I would recommend checking the Columbus OH market.