Neither of them is exactly bad but page ins you can't get rid of but page outs you can try to minimize with more RAM. If I'm talking bullcrap, please correct me
You're not talking bullcrap or "drunk posting" as spinnerlys sometimes does (he usually admits it when he does!

) The reason I said neither page ins or page outs are bad is there are many in this forum who freak out if their battery health drops from 100% to 99% or if their screen seems a bit brighter from one day to the next. It wouldn't be good for those folks to be obsessing over Activity Monitor readings, as well.
OK, I know everyone here is fairly computer literate, but I'm going to give my RAM explanation for the zero-computer-literacy crowd. I know it's extremely basic, so forgive me, but it might help a few who stumble on this thread in the future. This is not intended to be a technical "white paper", but rather, an explanation of the concepts.
Imagine working with paper documents on a small desk (small amount of RAM) and having the requirement that any page you work on requires it's own space on the desk (no stacking). All your documents are stored in a filing cabinet (hard drive) 3 floors down, accessible only by the stairs. On any trip to or from the filing cabinet, you can only carry one page.
You start with a clean desk (boot up) and as you start to work, you first must retrieve pages from the filing cabinet, one page per trip (page in). When your desk fills up, in order to make space for more work, you must first take a page from the desk (usually the one that's been unused for the longest period of time) and return it to the filing cabinet (page out). Then you have space to retrieve a page from the filing cabinet and put it on your desk (page in).

As you can imagine, with a small desk, you'll be spending most of your time running up and down the stairs to the filing cabinet. If you get a larger desk (more RAM), with more space for pages, you can make fewer trips to the filing cabinet, leaving you more time to do actual work.
1) Is it possible to keep computers running with an uptime of say several weeks without encountering slowdowns due to insufficient memory?
Yes, if you have a reasonable amount of RAM. In my experience, Mac OS X does a much better job of releasing RAM than Windows did. With Windows, frequent reboots were necessary to clear RAM and make the system run faster. I frequently run several weeks uptime on the Mac, with no noticeable degradation in performance.
2) Assuming an SSD is in place (in probably a better system than mine) and with memory still being a bottleneck, could one expect the same slowdowns? Or does running an SSD significantly help matters?
Having an SSD is like having a filing cabinet only 2 floors down, rather than 3 floors down. It's an improvement, but still not as helpful as more RAM.
a- How much would fragmentation of the HDD affect system performance? I was told that UNIX based systems don't really need to be defragmented compared to their Windows counter parts
In the overall scheme of things, fragmentation under Mac OS X is the least of your worries when looking to improve performance.
b- Does frequent movement of large media files (several GBs at a time) make fragmentation worse? I constantly download HD stuff from iTunes and after my HDD is almost full (with maybe 8GB of free space), I would move them off to my external HDD. The cycle repeats.
Again, Mac OS X does a much better job of handling fragmentation than Windows does, in my experience. However, having a small amount of free space can affect paging performance (imagine the filing cabinet almost full and having to take longer to find a space to file things, to be over simplistic.)