Only other initial question I'll leave here is that I'm looking for REI mentors and hope to find a few on BP willing to share a few gold nuggets to those willing to slog it out in the mines the smart or hard way.

Hi Linda,Lots of great advice from @Carla Gordon @Brian Schroeder @Jay Thomas Specifically I think it's always smart to check out FF Traveler sear https://www.furnishedfinder.com/housing/New-York/New-York) and Airbnb/VRBO for 30+ days stays to gauge what sort of similar properties are currently out there!

I don't think you're being too ambitious, I think its a very smart Idea especially in Chicago where there are an abundance of 2-4 unit buildings!

As others have mentioned, having a good ballpark estimate of rehab costs before closing is also smart, and likely required if using a hard money lender. 

Is it smart to take out a 40 year loan to get some cash flow?  

@Franklin PerezGetting your real estate license can be a smart move if you want MLS access, networking opportunities, and savings on commissions, but it comes with costs and disclosure requirements.

Is this something smart or doable?

@Christian Solis For a fix-and-flip business, structuring your venture as an LLC taxed as an S-Corp is a smart choice, providing both liability protection and tax efficiency.

Starting with an owner-occupied duplex is a smart way to build equity and gain experience.

As someone new to real estate, I’m curious if going this route is a smart move for a beginner or if there are better ways to start investing.