I’ve heard people bragging about going straight to the listing agent to submit an offer in order to save the buy-side commission before and found out that they overpaid by the property by $500k in order to save a $30k commission.

Well, if you can say it with a straight face, then you avoided recapture tax.Problem 2.

I would listen to the straight up Chicago investor podcast for local market knowledge and reach out to various guests that you think you'd connect well with. 

Really want to learn the wholesale business. I’ve gone out and found 17 properties all do owner financing 

There’s a lot of noise out there, and your post cuts straight through it.believe it or not I am asset rich and income light but it is because 1) I Believe in RE leverage so my cash flow is minimized 2) I am “retired” meaning I have no w2 job, my job is managing our assets.I am still in the hunt for a good RE investment but I am being very selective and most would consider my underwriting conservative (I hope it is conservative but do not think it is very conservative).  

Some DSCR lenders, especially smaller private ones, will underwrite based on actual income if you show stable rent history (usually 3-6 months).If you go straight to a conventional or big-box DSCR lender, they’ll likely discount the income or reject the deal outright.

Like @Andrew Steffens said, it might also mean that the surrounding neighbors -- used to some commotion -- might be less picky about STRs nextdoor.Plus, is the busy street a straight shot into the heart of wherever? 

I'd say that one investor's bad lender can be another investor's great lender.Some lenders are out to pitch potential borrowers on the "lowest rate", but when you get around to all the extra fees and costs not included in initial discussions, they're way less competitive than someone with a higher rate.Key is to always just straight-up be direct, ask the right questions about fees, costs, timing (I'd list this one twice for any kind of construction loan!)

Curious — are you leaning toward a duplex/triplex to start, or aiming straight for 4 units?

It seems straight forward, but I thought that I would ask here, since there are so many people here who have done a lot of off-platform renting.