Becoming Well Equipped
Time is the major component in this equation. The bare naked truth is just about everything in-game is a time sink of some sort. If you have the time to invest, you will reap some sort of reward.
If you commit the time to doing quest, running dungeons, leveling professions, gathering materials, and even scanning the Auction House for deals, you will be able to acquire gear.
Knowing what gear chocies are upgrades, side grades, optional, just get me by, and to be avoided is important. There is no reason to waste gold or time with sites such as Wowhead that do an excellent job of helping a user find upgrades for each item slot. You have to educate yourself. Ask other players questions. Ask for suggestions. Ask on Twitter. Ask on a class related blog. Get knowledge. Get the addon Pawn. It’s not bulletproof, but it’s better than being a dunce.
Understand what your base stats are and how they improve your abilities. If you are a hunter equipping gear with strength as a base stat on it you are doing it wrong. WE DO NOT USE STRENGTH. It will not make your pet any better. AGILITY. It is the answer. It is the only answer.
An addon such as Atlas Loot Enhanced can help you figure out what dungeons you need to do until you get your needed gear from it. The addon lists the gear that each boss drops. Is it a guarantee that what you need will drop the firs time you run the dungeon and beat that particular boss? No, but you can focus on running that dungeon instead of just picking something at random if there is a certain piece of gear you’re in need of.
As a side note to what I just stated; I do not agree with dropping out of a group just because the piece of gear you wanted did not drop from a boss. I do no agree with it, I do not advocate it, nor do I endorse it.
Check the Auction House to see if any upgrades available for you are crafted. May be you can craft them yourself or have someone else do it. If you are having someone else do it, be prepared to gather the materials that are needed. Don’t be a cheap skate. People’s time is worth something for helping you out.
Factions. Always check with each faction’s quartermaster. The quartermaster is your friend.
You have to pilot the gear upgrade process. You must be persistent about the task. It may take you one run of a dungeon to get a particular piece of gear to drop, or it could take you several runs. If you give up, you will not get that upgrade.