Should We Sue The Previous Owner

Hello!

I am considering hiring an attorney to sue the previous owner for our house, but I am conflicted because I know it is hard to prove knowledge of previous issues. I spoke with an attorney who made it sound like these cases usually get settled outside of court and that we would be likely to win, but I'm uncertain if he was just trying to get hired and would have said anything.

Background:

We purchased a house in spring 2023 knowing that it would have some issues. The inspector identified several issues, but we hired a contractor to do renovations and address most of the problems identified during the inspection so we figured most of it would get taken care of through this. We also got a discount on the purchase price and the seller covered closing costs through negotiations due to the bad inspection. The seller did not disclose anything on the sellers disclosure sheet.

Upon moving in and finishing renovations, we immediately started having several water issues. Water was leaking in through 2 separate sliding doors on the 2nd floor (the house has sliding doors instead of windows in each room) and we noticed a large water mark in the ceiling emerge in the 2nd floor ceiling below the door that goes out onto the roof. We had several handyman come out to try to address the issue and eventually ended up getting the roof door and all the sliding doors replaced.

Upon replacing the front sliding door, we discovered extensive rot on the front of the house. This was all replaced and taken care of, but the rot was so extensive that the contractor said we should consider suing. It was obviously going on for years and it's impossible that she didn't know about water leaking in through the sliding door.

Upon replacing the roof door we discovered about a 12 inches of rooted wood/beams immediately below the roof door and the insulation was removed. The inspector had also noted that there was bad drywall in this area, so it's certain that she knew about this issue. We think she may have had someone try to caulk the door to fix it, but it obviously was and she would have known about the rotted wood here.

The previous owner lived in the house for 30 years, and bought it a few years after it was build in the 90s so there is no other owners that could be blamed for the issues.

The last thing worth noting - when we did the renovations we discovered the previous owner had written a letter and put it in a bottle inside the door that states several years ago she didn't clean the drain on the roof and it caused several inches of water to build up and caused massive water entry into the house. They had to tear down walls and redo drywall because of this which is when she wrote the letter. This is not exactly relevant to these specific issues, but adds to the character of this owner. She even signed the letter!

We are in Illinois.

Thoughts? Should we sue to recover money for the window door replacement and having all of the extensive rot replaced? Or is it not worth the time and money?

TLDR; previous owner didn't disclose water issues she had to have known about and we uncovered rotted wood in several areas and have paid $20k for new doors and windows to fix the issues.