New site for truck parking

Here's my thoughts:
Bobtail, Tractor trailer & about 2 - 10 oversize spaces for those guys.
I don't know how many oversize spaces you'll need. That's not something I know about but I suspect the oversize guys here can give some input.

Cameras
This will add to not only security, but to catch mischief, who's dropping the trash, pee etc, as well as accidents to assist the victims.

Assign spaces
With assigned spaces, you know who stayed there in that spot. Damage or trash to your property as well as who dropped the trash there or backed into the truck in the next space. If your lot guy goes out and there's trash in the area, you know pretty much who to look at. You may not always see it on camera but if it continues, you could move the suspect or the guys on each side to other spots & see where the trash continues to be. There or did it move? Its not perfect but it certainly narrows it down. You'll know who the problem clients are in short order. You need to have them fill out a brief registration card & maybe a copy of their D/L for police reports, your insurance etc. Enter this info into a data base on your computer.
It also gives you a running total of how many spaces you have, where, for new or future clients.

Obviously good lighting

 

I'll add something else too.
You mentioned food or something, I didn't go back & look, but, if this is going to be for single overnight parking as well as weekend & weekly parking options, instead of you getting yourself involved with food (other than drink & snake machines), consider contracting with a few food trucks to come by at designated times... make sure there are more than Mexican food trucks. Some of us would want a good burger instead of a soft taco. Maybe a pizza truck. BBQ truck. Look around & see what your options are as far as who & what food is available to service your lot. Charge them a fee to come onto your private lot & sell food. Take bids. Or you could just contract with them for free if you're willing to do that, to serve your clients. Many options.
Let the food trucks worry about food regulations.

Try to group your trucks using the above mentioned assigned spacing.
Reefers, bobtails, oversize. Otherwise, general flats & dry vans etc can go together. Not many people like to park next to a reefer. No offence, just something to consider.