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I have been playing WoW for a long time...
But we'll try not to hold that against you... :)
I think you're making this more complicated than it has to be.
You have 14 days to decide whether or not you like the game, not to roll up the "perfect" character and take him to the level cap!
So pick something you'll be comfortable with and go from there.
Lets start with the holy trinity;
Tank - in LoTRO your basic tank is a Guardian
Healer - here abouts, the only full time healer is a minstrel
DPS - if you like ranged combat choose a hunter if you prefer melee combat choose champion
For the moment, lets ignore captains, burglars and loremasters since their role in game tends to be more complex and will probably take you a bit longer to get the hang of... UNLESS you really have a thing for pet classes (loremaster) or crowd control (captains & burglars).
Choose your race based on what you like the most. There is no real penalty or bonus attached to any race so you should pick the one(s) you prefer the look of.
Choose any server. In theory, you're only going to be around for a couple of weeks and for the beginning player they're really all just about the same.
If & when you start a paid subscription, you'll have the option to create up to 5 characters on each and every server in the system without ever deleting a single one, so what you create during the free trial will never be a factor in the future.
Don't worry about crafting, no one makes any real money from it in this game! There will be plenty of time after the trial to choose which money sink you prefer!
And when the character is rolled up and you're ready to actually play, it gets even easier! The opening section of this game is so well thought out and the tutorials so detailed, you'll be an expert long before your 2 weeks are up!
Good luck and welcome! But most of all, HAVE FUN!