Or, it may be in parks I usually don't do business in and move them to other parks I do business in that give me incentives (i.e. pay for moving costs, hookups, free lot rent, etc). 

Very bad idea.

I'd be happy to chat a little bit about various U.S. markets, and opportunities available south of the border.If you like the idea, then we need to pick a date, time and location. 

Is it possible it remove a homestead exemption and is it a good idea in the long run?

Sometimes I get so busy helping people buy properties I lose track of time. ;-) 

I am looking for advice on ideas around this / ways to make things more at ease.

As I read once, try to have your business efforts be cumulative, so you are not always fresh on the learning curve, where the risk is highest. 

There are some good people in business, but there are also nasty, hateful people that will cut your throat for few bucks.

I want to add that this rental business is for vacation rentals/short-term, rather than long term rentals.

For those landlords who take security deposits in City of Chicago, is a separate business bank account sufficient for the security deposit or do I still need to set up the special landlord account that requires all W-9 paperwork from tenants etc?