I didn’t have a new one, but I got it when I lived in Boston with just one underground parking place that couldn’t fit a truck. I didn’t want to pay to store a truck and trailer ($50/each is the going rate), and the van was only $5000 so it was cheaper than a truck+trailer. I didn’t mind that I couldn’t unhitch and just drive the truck, and it was supremely easy to drive (it was an International 4700 with 3/4 horse Imperatore body, so a medium duty box truck). I now have a Silverado 2500 and a 2h gn, and I like being able to use the truck for other things, but most of those things could just as easily be done with the van (perhaps just attracting a little bit more attention).
One drawback for me is that although it was very reliable, the few things that went wrong were costly to repair because it was essentially a commercial vehicle. All the parts were priced for someone using the vehicle to generate income, and designed to last a looong time. And I had to take it to a heavy truck mechanic, not just the regular shop. I was putting like 3k miles a year on the thing, so I never got the value out of the repairs I did. You will have the advantage of a new vehicle (mine had 340,000 miles on it!), but things can get broken or worn out and you will want to ask the dealer a lot of questions about who can service these things and what their warranty is like.
I don’t think you will get away with parking it on the street, especially if you have to remember to move it frequently. I suspect you will need to pay to store it somewhere, which can be a pain, especially if there isn’t room for it wherever you board. For every show, you have to pick up your van first, and it can be difficult (and costly) to find storage. Self storage places can sometimes accommodate them, but for $$$. I was sometimes able to park it cheaply at a mechanics (my BO knew the owner) and at another farm.
When I was truck/trailer shopping, I did consider a new van, but I ultimately decided I wanted to do the normal thing. Maybe in the future, I will want a van again. It was what I needed when I had it, and the new ones are so cushy!