I wouldn't say to completely trust a mechanic doing an inspection either. They can have ulterior motives. The one time I took a car for a pre-sale inspection, they wanted to replace things the car didn't even have. I've never had a good experience at a repair facility.
Going from a Yaris, you've gotten used to a vehicle being very easy to own. It completely spoils you. Going to just about any kind of van is probably going to be a pretty frustrating ownership experience.
It might sound romantic to own something with a cult following but for someone used to a car that just always works, it's not. Being in a strange place with a broken vehicle is not fun at all. It's usually downright scary. Some may be able to laugh about it but the overwhelming sentiment is: "now, what do I do?" Situations like that are enough to make you question your entire plan.
I agree that 16k is an awful lot of money, especially for an old VW. Sure, everybody wants one, and people pay crazy amounts for them but you're shopping for your home and transportation, not for a hobby collection. Most everyone has a fond memory about an old VW but many also fondly remember the day someone took it off their hands for them. My Dad owned several VW busses in his earlier years. Now, seeing one practically makes him shudder, thinking of the number of times he was white-knuckled at the wheel or how he couldn't find a solid enough jack point to change a tire. He just shakes his head when he sees what they're going for now.
I strongly recommend putting reliability and ease of ownership near the top of your priority list (are you sure you don't want a Toyota truck?).