This isn't about "how to" as much "how best".
I understand most sites with vanity urls have basic rules:
What other rules are important to consider for a site adding vanity urls?
What are common words that should be reserved to prevent confusion or abuse?
I'm going to begin posting what I've found so far.
Set Character Limit >4 characters
Must contain at least one alpha [a-z]
Optional Special Characters: ._-
user.name
= username
)user..name
)-user-name-
, .username-
)Avoid character confusion by preventing similar looking characters l,1
, o0
colbert
is registered, prevent co1bert
or c01bert
from also being registeredCase-insensitive
Reserved Word List
about, aboutus, account, accounts, add, admin, administer, administrator, admins, ajax, anon, anonymous, apache, api, app, apps, archive, archives, article, articles, auth, authenticate, authentication, author, backup, better, blog, blogger, cache, careers, cart, changelog, checkout, client, clients, codereview, compare, config, configuration, connect, contact, contactus, contributor, cpanel, create, css, daemon, data, database, deal, deals, delete, director, direct_messages, docs, documentation, download, downloads, edit, editor, email, emailus, employment, enterprise, explore, facebook, faq, faqs, favorites, feed, feeds, fleet, fleets, follow, followers, following, font, fonts, forum, forums, friend, friends, friending, ftpuser, games, gist, group, groups, guest, help, home, host, hosting, hostmaster, http, httpd, idea, ideas, image, images, include, includes, index, indexes, info, invitation, invitations, invite, is, it, job, jobs, json, lib, library, list, lists, login, logout, logs, mail, map, maps, master, mine, mis, misc, miscellaneous, moderate, moderator, module, modules, mysql, news, nobody, node, nodes, oauth, oauth_clients, offers, office, openid, operate, operator, oracle, order, orders, organizations, owner, password, passwords, plans, poll, polls, popular, post, postgres, postmaster, president, privacy, profile, profiles, projects, public, put, pwnd, pwned, pwnage, question, questions, qwerty, rdf, recruit, recruiter, recruiters, recruitment, register, registrar, registration, remove, replies, root, rss, sales, save, save, script, scripts, search, security, server, service, sessions, settings, shell, shop, signup, signout, sitemap, spam, ssl, ssladmin, ssladministrator, sslwebmaster, stat, stats, statistics, status, stories, student, styleguide, subscribe, support, supporter, survey, surveys, sysadmin, template, templates, terms, test, tester, testing, tests, testuser, theme, themes, tour, tomcat, translations, trends, tutorial, tutorials, twitter, twittr, unfollow, unsubscribe, url, update, upload, uploads, user, users, video, videos, weather, webadmin, webmaster, widget, widgets, wiki, www, wwww, xfn, xmpp, yml, yaml