How often should I upgrade my equipment?
I upgraded my armor as I found better pieces and/or made my own armor. You’ll feel the difference when you enter higher level zones/instances if the armor isn’t protective.
For dungeons, it is level 30. In my opinion, leveling beyond that and getting some good gear makes for a better experience. Story modes are easier than explorable mode; however, easy is a relative term
Map chat seems to be the place to find parties for dungeons atm.
It really depends on what you’re planning to do. In general PvE you can be fine with gear 10 levels below your current level. For dungeons however, you definitely want your gear to be level equivalent. Also, if you’re planning on doing WvW upgrade every 5 levels if you can. Your WvW stats are scaled based on the max stats of your gear to your level so if you don’t upgrade you’ll actually be getting weaker and weaker as you level up. It is extremely important to have level appropriate gear in WvW.
Fort Aspenwood
I’d recommend every 10 levels. Either by crafting your own or buying cheap stuff on the Trading Post.
I like to set aside a set of gear through crafting, as I often level the crafting faster than the character. For my Guardian I had a full level 30 set of armor, and a weapon waiting. I also have a set of 45 waiting for him in the bank too. I just fill in the other stuff from the TP if I don’t find it on my own.
If you’re just running around doing hearts all the time you don’t need to upgrade all that often, just use stuff you find or buy the stuff from heart vendors. If you do dungeons a lot, keep your gear fairly up to date, as they can be difficult enough without nice gear.
I’d say karma gear every other ten levels.