i'll answer your questions from how i approach it.
1 - depending on the circuit i try to make it as small as possible, while trying to have the least number of cuts and jumpers. the problem is, for me at least, sometimes when i make them as small as i can things get too cramped, and i don't want everything right on top of each other. i'm usually more concerned with having a lot of jumpers, but cuts don't bother me that much, some circuits it's inevitable and you're going to have a ton of cuts and jumpers, look at the orpheus.
2 - i try to make some rules to follow, for instance mark rarely if ever has standing resistors, i try to do the same, but if i want to cram something into a 1590a box, sometimes i do, or if i get everything done and one or two have to stand so be it (i try to go back and do a revision so that i have no standing resistors).
3 - i do try to get all the wires for the for each pot on the same side and near each other, but that doesn't always happen, for me not a huge concern for me though.
4 - i try to think of the strips as a road, and when i build i usually start at the input and move across the circuit in one path, then go back and start filling in other parts. for me it helps keep me focused, and helps prevent me from having parts cross where they shouldn't.
5 - when i'm don't i usually print mine out and use different color markers to trace specific paths and do the same on the schematic so that i can check all my work.
but like i said, make rules that you follow when making your layouts, and you'll be fine. it's a lot of trial and error. i would start with something smaller to get your feet wet personally, and what was suggested to me before was take a schematic that's already been done and make your own and compare it to what's been verified and posted here, like a fuzzface or rangemaster. just my 2cents.
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