There are usually quite a few wanted people, for two reasons.

Firstly, there are a lot of wanted people below the pk range of the lowest ranked tribs. This is likely to continue to be the case whilst tribs are numerous because the cabal membership will have a lower turn-over and thus generally be of higher rank. There are a lot of hoops to jump through right now to get into tribs and this will also mean that people tend to be higher rank when admitted.

Secondly is the Nihilists, and various other trib enemies who just don't give a s*** about whether they are wanted or not. These are the guys who will quite happily attack in town even though they know there is a trib on duty. There are quite a few of these.

Regarding Udgaard guards: Udgaard has it's own system of laws. It is a highly lawful city. As a result, they don't want the kind of person who doesn't respect legal frameworks.

The guards in the Feanwyn weald make plenty of sense. Have you ever looked at what they are carrying?

There are ways to avoid getting looted by a trib. I've turned myself in on a number of occasions and not once have I lost anything.

Finally, there are some very successful crims at the moment. Voronil being one example, although I believe he did die recently and lose his flag.

I think you worry too much about the effects of losing the wanted flag. Die to a mob just after ranking, and you suffer very little. Generally though, I'd just keep the flag unless I wanted to pk in town again, in which case I'd lose it. Once you know that mobs like Udgaard guards don't like criminals you can avoid them.

I do agree with what you say about taking the easy path though. e.g. the sudden surge of evil (in practice, maybe neutral in theory) rangers who group with conjies that appear around the time of sylvan going.