We are in the same boat you are, just starting out and trying to get this off the ground. We have looked at County Fairs, but not workable for us at this point as they are all at least 5 if not 7 days long and they require you to be there at all times.
I was wondering about the Ohio State fair in regards to that. I don't recall ever seeing a vendor being closed while the fair was open.
The hardest part we are running into is the insurance end of it. Not all insurance carriers carry this type of insurance. Plan a big block of time to deal with this part of the business.
I was looking at, I believe, an umbrella liability policy. Have you looked at something else?
As to the trailer, if you need all the bells and whistles, go for it they are good looking trailers.
My biggest concern is to be compliant with all health codes.
If you are handy
( I'm not:icon_blush and can do some of it yourself, or even if you are not the guy that is doing our trailer now is basically doing a turn key for us.
Where are you getting your trailer from?
We already have the cookers we are going to use so that expense is taken care of. Look in the competition thread and look for Plowboys trailer, it was made buy the same guy and is almost like ours. I believe Todd has a smaller deck than we will have on ours. But then again he can build them to any size I believe.
I will be starting this from scratch. I have a smoker but nothing I could put on/in a trailer properly.
Get friendly with your health inspector. Getting those areas down before you are running will make a good impression. Find out the requirements before you do anything. They are there to help you and are not the enemy.
Good luck!