I’ve been in similar shoes, starting out small and gradually building up to handling larger projects.

And I had a similar experience.It was cool that my tenants (roommates) paid for my mortgage.

I posted a much similar post in another forum and got a combination DSCR lenders (which is fine) and crickets.

Best way to start looking into this is checking comps on Airbnb, look for 30 day min listings and see how they're priced, who's booking (by checking reviews), how the best performing MTRs are set up.Start ups costs are very similar to STRs.

Diversifying can spread risk and offer multiple income streams.I once worked with a friend who was in a similar boat.

When they have a listing that are similar to properties I own, I want to be foremost in one's thoughts as the natural buyer.  

I’m looking to get a condo 2bd/1bath or something similar near rush, Stroger/CC hospital, and UIC (not just looking to attract travel nurses I promise lol).

Look for similar square footage, close by sold last three months.

Think I did around 50-60 total nights last year, and will likely do something similar this year...60-80.

Fast forward twenty years and (maybe a $100M in cumulative real estate transactions later) and I'm still advising investors on asset management, typically focused on real estate as an agent OR mortgage broker, but conversely with clientele of my own age group with similar goals.