Now, let's tackle it like a pro: Identify the moisture source causing the mold, fix it to prevent a comeback.

The most education you will receive is when you do your first deal...surround yourself with investors and agents that are investors themselves to help guide you and prevent you from making any major mistakes and you will be fine....there will always be several things that you learn from on your first deal!

So as far as informing them, would I put this in the contract informing them and having them initial and sign stating I informed them and provided the necessary items to prevent such an incident?

The reason for this is that you end up taking a short-term rental to pull in a few bucks and that ends up preventing someone that would have wanted the place longer.

It has taken in water in the past however the root of that issue has hopefully been addressed adequately at this point. 

Prior to purchasing the beach house my credit rating was 720 and of course after buying the house and running up credit card debt my credit is now below 600, which is preventing me from refinancing the house.  

I have personally done both sides of things; ran PM biz grass-root's, and ran PM brokerage in a franchise system, a big BIG name one. 1 universal truth that stands in BOTH is your primary existence as a PM, franchisee or grass-root's, is that your a full-time "vanguard" of defending against the "WTF's" and in being a "Fire-Fighter" putting out the "fires" of the various "WTF's" that happen.     

I am curious as to what root causes have decreased the Chicago inventory more than other major cities. 

If this was me, I would be at the property, getting in touch with local Facebook groups and generating bids to get handymen/local contractors taking up urgent jobs that are preventing units from being rented (even at a lower premium) that are ready to help nurse the deal.

We are selling 2 buildings this year so we will need to dump quite a bit into these 401ks to prevent our income from hitting the threshold which will trigger our paying back our health insurance premium subsidy of $18,000.