Should we encourage upvotes on more advanced questions, that are seemingly well written, even if you don't understand it? ... Is this good behaviour? Should we encourage upvoting seemingly well-written questions even if you don't understand it?
The lack of voters for some questions is discussed here: Why aren't people voting for questions? - at length. If it's a bad question it should get voted down, if it's a good question (see: How to ask a good question?) it should be voted up. If you don't know don't be embarrassed (no one knows) just move on, you don't want to upvote nonsense.
It would be great if there was an "Interesting Questions" Tab that Mods and a group of designated experts could tag questions for, so the question would get more exposure (without necessarily having many views or upvotes).
If Mods could be given a "Bounty Wallet", so they could add a bounty to a question without pulling the cash from their own pocket, and a question received an "Interesting Question" flag from a single person (from a small group of designated experts), the wallet could supply a couple of hundred rep to at least get the question some views.
The actual upvoting should be reserved for the so-called "good question" (as understood by the voters).
A prime example is some people can take a good photo or are skilled at Mathjax, that doesn't make the question they ask useful or good. Some people need help taking photos or using Mathjax, that doesn't make their question bad or not of general interest; unless it's a FAQ or dupe.
A means to toss a 'good question' with few views or voters into an additional Tab, even to push it into the "Hot Questions" (when it's cold), would be helpful.
Voting for things you don't understand (up or down) puts an odd spin on the ball. You wouldn't wash your neighbour's car if it looked dirty, walk their dog if it looked lonely, take their wife out to dinner if they appeared hungry - if you shouldn't mess with stuff you don't know about then don't.
Those points were made in the links listed, if you're going to answer why not upvote the question, if you choose an answer why not upvote it also. If you don't know that's OK, but adding random votes or answers doesn't help the majority.
Unfortunately the asker will have to ask 'popular' questions for more votes and easier questions for more answers. Spending 10 minutes to get 10 rep is something each must decide for themselves if it's worth it.