Here is a list of issues with adding an ADU:1) The value added by the ADU addition is often significantly less than the cost of adding the ADU.

On another note, I had a lengthy conversation with VRBO last night while we both looked at one of my listings and came up some ways to improve it. 

I will include those banks on my list.

He’d likely play the role of buyer’s agent, contractor, and rental listing agent—something we successfully did last June.

I love that you have specific goals for 2025 - I believe if we think it, write it, say it, and share it our goals are 10x more likely to come to fruition.Are you able to do option 2 and just house hack a 2-4 unit building and use a renovation loan which allows you to put down 3.5-5%I highly suggest getting to some local chicago meetup groups (we have an in person one on the 17th)...here is BPs list: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a full list of the chicago meetups that I can share with you too if that'd be helpful.

It's been a few years since I last updated the list of providers (there are older threads on this topic here on BP), but at last blush there were five trust companies offering the ability to write and service mortgages from registered accounts:B2B BankCanada Western TrustOlympia TrustEastern TrustCommunity Trust CompanyOf these, Canada Western and Olympia has the best offerings at the time.  

I've personally done just about every rehab scenario, properties I've lived in, properties bought as investments and even properties bought at auction.You've gotten good advice from folks on this list.

Your list is more important than you realize3.

You claim my critique is “negativity”, when in actuality it’s a listing of incorrect assumption statements in your post.  

I would do the work of manually looking through other listings in your area.