Really a tailor's question in the end but a few thoughts. On getting trousers caught in the shoe, I just don't think there's a way of avoiding this with a fairly slim profile because one walks around. Hems will settle as hems settle, and I wouldn't expect that they always fall cleanly. It might be that a slightly wider hem will help, but you should expect that this will happen. I find my trousers sometimes gets caught in the back! But cuffed trousers that are skimming the top of the shoes should alleviate this issue a bit. I wear mine uncuffed with a touch more break. If you want your pants to hit right at a certain part of the shoe, why not take that measurement to figure out how wide your hem needs to be. Hitting the middle of the laces seems a good goal. Go to a department store that sports straight fit trousers which will be wider, more likely. See how they drape. Best way is to try some different fits out. Bring a tape measure and then take some measurements (go to a place with different trousers sizes, department store). I think that walking back a little from standard "slim" fits will help. There's a nice picture of a person in the HY thread who has the USA fit trousers. He was uncomfortable in their "fullness" but honestly, they looked Vox-like (i.e. like that pic above). If I can find it, I'll post it but you might look in that thread. I think we've sometimes taken "slim" to the wrong extreme.