Upgrading from Toyota Sienna AWD — truck+trailer vs. Transit? High roof vs. low roof?
Current setup: Toyota Sienna AWD. Works fine but I’m outgrowing it. Ready to upgrade.
I service the Bay Area (SF, Oakland), Napa, Sonoma, Sacramento, and Lake Tahoe — so I’m dealing with everything from dense city parking to mountain passes.
Two options I keep going back and forth on:
Option A: Pickup truck + enclosed trailer
Option B: Ford Transit (or similar cargo van)
For those running the van route — high roof or low roof? I love the idea of being able to stand up and load/unload without contorting myself, but I’m genuinely worried about parking. SF and Oakland have a lot of garages with low clearance. Finding street parking that fits a high roof van in dense neighborhoods sounds like a recurring headache I don’t want.
Questions:
1. Truck + trailer people — do you regret it? Backing into venues, parking in tight lots, disconnecting just to park somewhere… is it worth the flexibility?
2. Van people — high roof owners specifically, how often does clearance actually bite you? Is it manageable or is it a constant thing?
3. Any van models besides Transit worth looking at for this use case? (Sprinter, ProMaster, NV2500, etc.)
4. AWD/4WD matters to me for Tahoe runs in winter — how are you handling that?
Appreciate any input from people actually gigging in metro areas.
Appreciate any insights y’all have!