Once you move to Chicago, look for similar groups—Chicago has a vibrant real estate community.Building a Team: Since you’re new, connecting with a knowledgeable real estate agent, lender, and property manager in your target area is critical.

But if you have good credit, and this is a conventional loan on an investment property that is a SFH - you should be getting a lender credit, not charged points at 7.125. 

I do not worry much about "hurried or sloppy work" because it is also in my contract that all work must pass inspection, which may include the city / county (for permitted projects), lender and myself.

Sellers worried they won't be able to sell in time before their lender takes action. 

No (institutional) lender will finance 100% of your purchase price as a purchase, all lenders want "skin in the game".

Building an ADU is a nice way to add value but you won't get that funded by a lender. 

The best scenario for the buyer buying subject to is to have enough money and good enough credit to qualify for a new loan at current rates should the due on sale clause be invoked by the lender  

Find a lender that works with a lot of investors in your market and have a conversation with him.

A couple questions:1) Has anyone worked with local lenders like a local bank or credit union?

If you do a good job and make the private lender happy they will want to do this again.Then there's seller financing which you see a lot with businesses, and commercial property.