Can I have help with a Library situation?

I happen to be going on vacation in a week and a half for about 9-10
days and we are driving so it's going to be a long car ride. I have a
portable DVD player so I want to get a few seasons of the tv show
"Friends" from the library. I'm thinking seasons two and three. You
can check out up to six DVDs at a time, so that's not a problem. There
are two items to checkout for each season, so you get two of the four
discs with each checkout meaning I can take up to three seasons. I
want to make sure I can get all of the seasons I want at the same time
so I can watch the episodes in order. I'll watch the first season
before I leave and I already have the first DVD. Right now someone has
the second dvd of the first season but you can only have it for a
week, but you can renew it up to three times, unless that particular
item is on hold. also DVD 2 of season 2 is checked out but season 3
and 4 is all currently available. I guess my question is when should I
put the DVD's on hold. I don't want to pick them up for at least
another week because I don't want to have to pay any fines in case I
can't renew them. Do libraries usually allow items to be on hold and
ready to be picked up for more than a week? This is a very vague
question, but help with any ideas or opinions, thanks!