Empty the property, clean it up, start fresh with a competent property manager that handles these issues so you don't have to.Remember: cheaper doesn't mean you'll make more money.You can start by going to www.narpm.org to search their directory of managers.

If none of that was done, you just made a $50 voluntary donation to someone....I suspect it will be a matter of time until the individual that received your "donation" receives a visit from the FBI for wire fraud. 

These costs for most of the individuals are considered personal in nature( unless you have RE portfolio that is run like a business- see below).

I am new investor in Chicago looking to connect with other like minded individuals.

I'm selling them individually and have the first contract. 

So, your LLC could be the agent for the landlord trust.Recommend you seek legal advice on this from a competent real estate attorney.

They finally felt they were ready financially, but they were worried about the problem I just mentioned: they could get top dollar, but how could they compete for a new larger home?

If you're planning to resell and they're all on their own individual parcels, you'll have to figure out what they're worth individually if you were to sell the land with the mobile home on each parcel. 

Do I have to call an Insurance company with the property address for every individual property every time, to get that estimate? 

Lets not forget the sea of individuals who are making fraudulent claims, collecting tens of thousands of dollars at one time.