The main drawback of Prowling is that your party cannot Prowl with you, so using Prowl in combat to your advantage renders the rest of your party members all but useless. To sneak into some crowded place, you have to each time leave your followers outside. If you get a nice fight in there and level up, your followers don't. So I was thinking of making an Educator character+Prowl+Melee+backstab, plus followers with Prowl. The problem is there aren't many followers like that, and neither of them is a healer. The obvious solution is dressing my party up into Oiled Thieves Leather, which would give them one rank of Prowl. But that's only one rank, that allows for an Apprentice status. How useful will it be?
If you have someone in a cloak of shadows that boosts prowling based on their MA, you can gain up to two levels for them. Toss in a necklace or ring that gives you 1/4 of a point and thats enough for them to get expert. This should work well enough for you to get a healer with some basic prowl skill.
I'm pretty sure that your follower's prowling skills has no effect on anything. I've succesfully prowled past guards with Virgil behind me in full platemail. The guards only react to you.
IIRC, if any of your followers are detected by monsters, then you get pulled into combat too. So if you want to be able to sneak your way past combat, you need followers with high prowl.
Hmmm...I'll have to test that. Really, though, it doesn't matter, because who plays a thief with many followers? It isn't realistic.
Also, does the Oiled Thieves Leather gives a rank in prowling as a guy suggested here? I thought that a specific type of robes is giving the character this bonus.
I believe it gives 1/4 of a rank on Prowling, Spot Traps and one or two other skills (don't quite remember which)