You can check an option under multiplayer -> advanced to "remember last weapon between lives". That should make it easier to keep "Q" rotating between your preferred weapons -- You'll only have to swap between them once, when you first spawn as that class.
Most items have a set number -- before the Scout update introduced the Sandman, no item went higher than level 10.
About the time of the Spy / Sniper update, there was a glitch in the random drop system, and normal weapons (that usually have a fixed level number) were generated with a random level between one and one hundred. This has since been fixed, so if you see, to use one of my own items for example, a level 56 Dead Ringer, that means the item is very old. (And now with the latest patch, you'll never see a non-vintage oddly leveled item)
On the other hand, hats will always have a random level. This means nothing, but certain levels are certainly more valuable for trading, for pure sentimental value. (1, 100, 69, 42, etc.)
The singular exception to all of the above is the new Dueling Badge medal misc item, which actually "levels up" as you kill folks during your duels. A level 100 dueling badge works out to 1000 kills (Might be off a factor of ten) during duels, and likewise the rarity of the badge itself (bronze, silver, gold, platinum) is based on level increment. 0-25,26-50,51-75,76-99,100, etc.
In no case does the level of an item have any effect on gameplay.
Best Answer
Any item which could have an effect on the game can either be found as a drop, unlocked from achievements or be crafted.
The only items which cannot are reskins of certain weapons, some cosmetic items and Strange (kill-counting) Weapons. Most of these are promotional items from other games and all behave the same way as an acquirable weapon.
A full list of items which aren't dropped can be found here: http://wiki.teamfortress.com/wiki/Item_drop_system#Non-dropping_items