After closing out of any program(especially Adobe products), it would hold onto 4-5gb of memory allocated specifically for that for hours at a time. Only way to free it up was to reboot or go into memory management and free it up. And just in case youre wondering, yes, i was closing it down properly, not just minimizing it and thinking ti was closed like so many people who i have come across that use macs think.
I hate to ask, but are you certain you were quitting the apps (App menu -> Quit / Command-Q)? There's a big difference between minimizing an app's window(s) and quitting it, certainly, but there's also a big difference between closing an app's window(s) and quitting it. Most Mac apps will continue to run happily even after you've closed their last window, very unlike Windows apps (this includes Adobe apps). If the process was still appearing in Activity Monitor (or top in the terminal) as taking up X GB of memory, then you didn't actually quit the app.
Tried Mac in 2013 for 6 months, not an awesome experience. Never freed up large amounts of memory unless i did it manually, adobe products temp files took up 130gb and not intuitive to find and delete, little things like single clicking on a long file name to see the whole file from the desk top or even finder was impossible. That was important to me since my photo file names are usually pretty long(Latename - date - sequence). It didnt work for the way that "I" work so it wasnt an option. Plus, bought the MBP maxed out for 2500, couldnt sell if for more than 1300. Complete waste of money and time for me.
If you didn't like it, you didn't like it, and that's fine... you should certainly work using whatever tools you feel most comfortable with. But your specific points I don't get.
Why are you trying to micromanage memory usage? This isn't the 90's. The OS will free up memory when it is needed. Any memory that is just sitting around "free" is memory wasted. The best way to check if you're running into memory constraints is to check if the OS is using swap at all (Mavericks has a nice memory pressure graph too, though in 2013 you probably did not have Mavericks).
Adobe software sucks, but it should be cleaning up its own temp files except in rare circumstances. I've never had orphaned temp files in the decade+ I've been using Photoshop and Indesign. Still, if they're a problem, you only need to learn where they're stored once.
The easiest way to view long filenames is in list mode. If you're looking through a bunch of files with long filenames, it's stupid to do it in grid mode, where you're obviously constrained by the grid. The desktop itself is grid-mode-only, but the desktop folder can be viewed in a Finder window like any other folder. And if you must - hover your mouse over a truncated filename and the full thing will pop up as a tooltip (if you're navigating through the files with the keyboard, hitting enter or return will show the whole thing).
And your resale value - obviously this varies from place to place but a Mac about a year old should sell for at least 2/3 its original value - $2k or maybe even $2.2k would have been more than reasonable for a 6 month old Mac. 1/2 the original value is more common for a 2+ year old laptop. I have a number of friends who do the sell-and-upgrade cycle every year or two and it works quite well for them (though I personally don't find it worth the trouble). If you live somewhere where the local resale value is low, just use eBay. Based on the price, I assume this was your Mac, and now at >1 year old they're going for $1800.
Where there's a will, there's a relative.