@Johnny McKeonI'm not a CPA but my experience says, yes, you probably can.To avoid confusion it is helpful to separate out the concepts.REPS - Roughly, the requirements are minimum 750 hours active in real estate and those hours must exceed any hours in a non-real estate job.  

I’m also looking for mentorship, partnerships, and apprenticeship opportunities to sharpen my skills and learn from those who’ve been there before.If you’re an investor, agent, lender, or property manager in Milwaukee (or have experience with multi-family and house hacking), I’d love to connect!

What’s been your experience with real estate education programs?

Their experiences could offer valuable insights and strategies to help you navigate the market.Good luck on your journey! 

Both options have pros and cons, and the right choice depends on your lifestyle, experience, and long-term goals.

Does anyone have experience with this?

The best way to get experience is to do the thing.

Now you are saying you have no experience owning/operating an STR, that's another hit.  

House hacking and basement conversions have worked in my experience. 

Lots of great info on here as well, and like they're saying the best thing to do is to find an experience broker / realtor who can help you navigate which neighborhoods to target and which ones to stay away from, as well helping you to build out your team for property managers, lenders, inspectors, contractors, ect.