D&D 5E Desperatly Seeking help

First, WELCOME to EN World! Have some start-up XP! :)

Second, I have a couple of questions:
1. According to your apparent game intro from the DM, you are supposed to be from this city. So your druid concept doesn't really quite fit. Not a huge stretch to say you're a druid from outside the city, but still, I'd lean toward your paladin character.

2. What is this "guild" he keeps mentioning? It sounds as if you are assumed to already be on a track to work for them...and seeking membership? It sounds,from Reuben's "introduction" like an assassin's guild...in which case why is your paladin, concerned with/devoted/defined by his oath to his own vengeance, interested in being involved with it?

3. To reiterate (maybe in a slightly different way) what others have said, don't be so down on yourself. The backstory ideas you have had are just fine. D&D is a game of imagination...long as you have some imagination, you're doing just fine. I would, however look to Blackwarder's questions above and come up with the answers to those questions. I would also agree with those saying not to worry about building anything too "deep" in terms of backstory just now. 5e gives you Backgrounds to choose, what are your character concept backgrounds? That can give you a lot of direction and inspiration. Again, these obviously have implications for your past and it sounds like your DM is under the impression your past is just in this city...?

4. To be clear, I do not think the onus is on the player to meet the DM's game story assumptions, but at the same time, if a setting is established, then you should do your best to make sense within the setting (as far as its been established so far). i.e. Don't bring a druid into an urban adventure.

5. AT THE SAME TIME, I do not believe it is the purview of the DM to tell the players what their childhood was/where they are from. So, kinda a strike against your DM to [try to] dictate "you are from and spent all your life in this city." That's poor DMing. Plopping the group of disparate characters into a setting and saying "You all have reasons to be here/figure out among yourselves why/what your connections are" is one thing. Plopping a group into an adventure saying, "You're all from this city. You're all part of this guild."...or even, "WANT to be part of this guild" is a step too far, from my DMing perspective/sensibilities.

ANYWho, welcome again and have a great time with it. As for why/how your High Elf Paladin or Wood Elf Druid would be in this city or interested in this guild...that's really up to you. Since you are asking/looking for some help (I'm not going to write it for you! Kinda like doing someone else's homework. hahaha.), off the top of my head, how about something like:
1. This guild has information on the Dragonborn band/tribe/individual warlord, whatever that killed your family/village/whoever. So you are looking to work your way up into their ranks in exchange for eventual access to this info. A little thin. Not sure how long your character would be willing to do "errands/missions" for this mysterious guild without some useful info.
2. For the druid...ummm...There is reputedly an alchemist/apothecary/herbal specialist [and expert poisoner ;) ] who works near-miraculous potions in this guild and you have agreed to this, initial/primary mission as a payment for a meeting/consultation with him[her].

Neither of these are reasons for you to be there, or stay with this guild beyond the primary adventure/mission. And that's fine.

Keep in mind also, this is a GROUP endeavor [and game, as a whole]. Your character needs ideas/motivations not just to be where they are [which apparently your DM is dictating for you] but WHY you are working with these other adventurers. Naturally, some of this can be done with the other players directly..."How about my character and your character are <childhood friends/siblings/lovers/former adventuring companions/related some other way>?" And some of it can be handwaved as "We're all working for this guild so we're all clearly 'on the same side'" but beyond that, a reason to STAY with this guild/these people needs to be present [probably by the DM].

I bring that up because both of your concepts sound, very much, like loner/individual-type personalities. "I'm on this [even 'life or death'] mission that is important to me!" Once you've finished the first adventure for this guild [with this dwarf who is apparently your "boss"?!], your pally is still looking for his revenge....your druid is still looking for her remedy to the darkness consuming her wilderness...Neither of these folks sound like they're interested in sitting around "employed" in this guild for any amount of time.

That is perfectly FINE, from my perspective, but from your DM's it sounds like you are expected to remain a part of this guild and do stuff in THIS city. So I would get that clarified before putting too much time or effort into a finely crafted backstory...which, ultimately, as others have pointed out, are best "developed" in/through play than set in stone before the game.

Get an idea of what, if any, remaining family these people have. Why they're in this city. Why they're interested in dealing with this guild/and or willing to be supervised by some psychotic murderous dwarf. As I said, there are many ideas brought up through the Backgrounds with their "ideals, flaws and bonds" so they should give you an adequate jumping off point.

And, MOST importantly, as always, HAVE FUN with it and happy gaming.
 
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Another reason is that if your character happens to get killed early in the game its kind of a wasted effort.

This is a good point. I don't know how deadly your campaign is OP but our group started a new 5e campaign 6 months ago and I've been through 3 characters already. My backgrounds started out pretty detailed. Now it's just "Haszlo enjoys the simple things in life. A laugh, a pipe and stabbing bad guys in the kidney." Maybe once we get up a few levels I'll flesh him out a bit more. For now, I'm just gonna leave it open.
 

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