But I started at a different time in the market cycle, and attribute my success to date to luck and caution, mostly to luck.

Please let me know if I can bring any value to you about the markets I've referenced.

what would make more sense in the current market right now ? 

Assuming your market is similar, I would add an ADU not primarily as an investment.  

Hey @Jake Wosick - You should definitely connect with @Zach Shepard above, he's been a great mentor for me and knows the off-market chicago space better than most.In my opinion, the key to off-market deals is understanding the ROOT issue with the seller. 

Get it back on the market and move forward. 

Hello all, my name is Brian floyd and Im a fresh back into the real estate market since 2021. 

Looking for suggestions on co-hosting, STR market analysis, RE investing for or in retirement - just reading anything I can get my hands on in my (late in life) RE journey.

You will just be capped at the price you paid for the property as your loan amount (which is not typically an issue unless you are buying well below market value.) so, if you can truly get a better deal on the property by paying cash it can make perfect sense.

That is pretty standard in my market and if I am not mistaken it is more like $25 dollar add on here roughly.