The deals not going to get better because of the questions you ask, but we look for three main things from an investor: 1) Liquitity/Financial Assets, 2) A good credit score, and 3, and this is a big one, Experience.

Thus a great opportunity to be a part of it financially!

As wholesalers, we’re trained to look for distress—motivated sellers in tough situations, properties needing major repairs, or financial struggles forcing a quick sale.

If there is even a small chance, I would disclose.If I remediated the water issue and confirmed it's no longer an issue, then I would not feel the need to disclose that.Talk to a Chicago attorney to get the best answer....who would ultimately be the one who would defend you in court...when in doubt, disclose, and you'll be better off.

These things going to court you have to Steel Man the argument and if you can do that with a good base for your side being in the right/wining the argument then you may be able to win in court.

If the tenants take legal action, a court could find that you didn’t fulfill your duty to mitigate damages, leaving you responsible for the full rent.

I've been a financial planner for 17+ years and one of the main umbrella theories I've learned is that often times, the simpler things are the better they are. 

Those special assessments will not be enough, and the reality is the association will likely be taking debt to approach these projects (eg. paving the parking lot, residing a building) and that financial burden would be on the owners and the association. 

A recent article discusses how Bloomington is considering flexible zoning to support dorm-style units, aiming to provide housing solutions for residents earning 30% of the area median income (AMI). finance-commerce.comThe city has successfully added new rental units in the 50% and 60% AMI bands but faces challenges in creating units for the 30% AMI bracket due to financial constraints.

While a more robust conversation around your entire financial picture would be required, here are a few questions that I'd want to double click on first:Where is Your War Chest?