I agree with what everyone said. I play a Paladin tank and a raid cleric. I will be the first to tell you that in group content I would much rather be healing an SK. That said warriors and paladins are suitable for your needs.
I usually stay an expansion or two behind (although I am almost done with current content) just to make the game more enjoyable. I don't like banging my head against the wall trying to beat a mission that requires uber gear to beat, My pally is actually in uber gear now (mix of ToL raid and ToL TS). I would recommend the 100 heroic toons if you have the disposable income. Someone mentioned the bags and the AA's, but they forgot to mention the amount of PP saved from not having to buy all those spells, not to mention the time saved from all the skillups. There is a nice macro on this site that will do skillups for you, but if you go the heroic route for the other goodies it will save you time.
As for not knowing what the toons are capable of doing or how to play them, just think of it as level 100 being the starting point. Heck before 100 it is really a different game anyhow. Take your level 100 any House of Thule zone and learn it there.
My choice for servers would be live servers. Like mentioned before the nostalgia is nice, but the drama is real. I felt like I was back in middle school when I tested out Mishief server. I really loved the idea behind the server, but they did not mention that it is a truebox server and I am not buying 5 more PC's to run a crew. I recently started a crew on FV and I am liking it there. I love how most everything is tradable and the permanent 50% exp bonus makes leveling a lot less painful. The economy is crazy there though, but you won't notice it because you are not used to any server's economy.
As mentioned you will be able to run some older raids with your crew, but in all honesty raids are going to be something far off in your future. Gearing up 6 toons is gonna take a long time. Don't be fooled into thinking "Oh great I have my own group and I am gonna crush the content" You will do better than your average pickup group because all of your toons will be doing what you want rather than relying on other players that go afk, faceroll the keyboard, or just don't have your play style. You will need to farm augs, clickies, armor, weapons, and AA. All of these take time because of well you have rare spawns to wait on. My question to you would be how many hours per day do you plan on playing? If we are talking 3-4 hours per night I would not expect to raid anytime within the next year or two.
When you finally make your crew make sure to make a fellowship and get them all a fellowship clicky device, it will make your life so much easier because you will wipe it will happen just prepare for it.
I like your group makeup as a starting group. Just know that you will tinker with different classes and eventually settle on your preferred group. My preferred group for most things I do is Pal, Brd (I hate brd and might learn to love it when Sic and CWTN are able to make a plugin), Zerk, Zerk, Zerk, Clr. With this crew I can destroy a lot of content, yes I run into issues, but I like this one. I sometimes go Pal, Enc, Zerk, Zerk, Bst, Shm (This makeup drops my fights by about 8-10 secs per fight in most situations and the Enc imo is WAY better than the Brd at CC, but that is mostly because I have no idea how to Brd and I played Enc for years. I prefer my Clr over Shm because well Clr is raid geared and Shm is ToL T1 group geared (Shm is on ftp account and Clr is gold).
When you finally reach max lvl you can do all of the group content. Your group makeup and gear will determine how difficult that will be. I can currently run the first ToL mission, but I have to replace the Brd with my Enc (for some reason my
kissassist ini for Brd doesn't want to mez the adds so I just roll with the enc and I have a key on my Pal that tells the Enc when to AoE mez. My clr, using CTWN plugin only cures when it feels like it so I just handle cure using the Pal. I get totally destroyed on the other missions right now so I am going back to the gearing up phase to make them better. I am very limited by 4 of the 6 being FTP. If they were Gold with real gear and augs it would be a different story.
One of these days I will look at the Brd's ini and figure out what it is doing.
Welcome to Redguides. Once you box using MQ2 you will wonder why you didn't find this stuff earlier. Nobody likes logging in and spending 30 mins to an hour LFG. We have all been there and if you are like me, you log out after 10-15 minutes or go play your Nec because he can solo. Do not be afraid to ask questions. Post accomplishments and be an active member on the forums. They really listen and are helpful. Sometimes people will sound like they are cold and offputting, but they really aren't.