In 2005, a little of 2006 and near the beginning of TBC, I suffered from the same problem many of you in this thread are describing, and that is the lack of a satisfying guild but having an insufficient amount of connections to improve your situation.
Originally Posted by sveno
The problem with applying to a guild that can gear you up is, if they don't know you personally, or you know noone in the guild, they're not going to gear you up. And the problem with applying to a progressing MH/BT guild is, they can't gear you up. So you'd probably be best off just getting the best badge/craftable gear you can, and maybe try to build some contacts with good guilds on the server.
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It's true that getting a guild to gear you up without knowing anybody in that guild is definitely a difficult task. Before you can manage to convince them to do so, you must have some very powerful evidence to put forth that shows you are worth that given guild's time. Such evidence required can vary by quite a bit, depending on the guild you're applying to, and their demand of your given class. Knowing what most of the leadership in many top-end guilds want is the first step.
Being part of leadership in a high-end raid for over a year and also having recently been accepted into a guild as a completely blue-equipped reroll, I'll explain what would be important to me if I were to accept a reroll. You must realize that with the elimination of attunements in WoW, the process of gearing somebody up is much much easier than it ever has been. As a result, this
task of rerolling to join a new guild is more realistic now than it ever has been.
High arena ratings are definitely a strong indicator of a player's personal skill, while some high-rated individuals can be carried to an extent and that many skilled players out there don't arena beyond 1600 rating, this definitely carries some weight.
Go over the top and go in-depth describing your class and your role, how you gear/play etc. The more thorough you are in this task, the more impressive you can come off to be. Be sure to justify any questionable spec/gear decisions you've made in your current armory profile. Answer questions before they're asked.
Evidence that shows high attendance in the past. This can usually be shown through links to previous DKP/Loot History sites that you've been a part of. An ideal example is two links to two different dkp/loot sites of previous raids both showing your name and 99% attendance next to them. While this is somewhat unrealistic, this is the ideal. Again, be sure to justify gaps in attendance.
If you're applying somewhere, it means
you're also willing to leave your current guild and/or raid. Depending on the guild you're applying to, this can be a very important determining factor for them. If you're disloyal to your current guild, who is to say that you'll be loyal to the guild you're applying to? Be detailed in describing the specific events/situations that led to this dissatisfaction with your current raid/guild and state why this is likely to never be the case in the guild you're applying to. These reasons can be extremely different, everyone has their own story.
How impressive you can be in all of those tasks usually determines how strong of a guild you can get into.
You must understand that luck plays a huge part in determining your application's validity to a guild. Mostly relating to the demand of your class to the given guild.