I'll try to make this as to the point as possible to cut down on random reading because I have a lot of questions. Thanks to anyone willing to help me out!

1. If I understand correctly, creating a new guild/faction is extremely easy. Put in all the info and call it a day. However, I'm not sure I understand how a guild's questline is built. Is there a tutorial that explains how to build from one quest to another and give increases in reputation as well as rank when the necessary requirements are met? Or is it basically the same idea as any other quest, where you'd make a quest and then the second quest would have a check to make sure you've finished the previous quest before allowing you to start the second? God, I hope that makes sense.

2. I'm going to assume it's completely possible to add onto an existing faction and with assumption, I'm going to assume that making the Twin Lamps joinable has already been done before. However, I'm going to use that as an example - though I'd like to be able to make all unplayable guilds playable. Using the Twin Lamps: How do you create the joinable guild without causing problems with the Hllaalu quests? Would it be easiest to make the two Hllaalu quests pre-reqs to actually joining? Like... You free enough slaves, you get the password, talk to whomever and get the Twin Lamps quest, finish quest, get second quest to free whomever, finishing this quest would then have Dren telling you to go seek out someone else to continue to do work for the Twin Lamps and talking to this new person would then give you the option to join the Twin Lamps. You'd avoid conflict with the Hllaalu quests but still make Twin Lamps joinable and I have a feeling that a secret - very very illegal - guild would require proof before allowing you to join anyways which would play into a RP standpoint.... right? Or am I totally incorrect? lol And if all this is possible ... where do I find the place to add the extra topic to Dren to bring up the statement to go seek out the new person? That's something I'm not too clear on.

3. And last, this is completely not quest related: Is it possible to create something like Azura's Star - a refillable gem - but have it completely heal your health, magicka, and fatigue when used instead of healing weapons or enchanting? And I'm going to assume it's impossible to have it linked to a certain weapon so that only that weapon can fill it instead of any soultrap spell?

I'm not very good at explaining what I'm trying to do so I truly hope someone can understand what I'm saying. lol Thanks for any input!

1: http://www.morrowind-oblivion.com/morrowind_cs5_tutorial.php and http://www.morrowind-oblivion.com/morrowind_cs6_tutorial.php are all about how to make a Faction and create the dialog variable progress for a Faction/Guild.
They do assume you're already familiar with creating Dialog.

2: How you want to implement the quests and join the Guild is really just up to how you want to the story to unfold.
To add new topics to an NPC, you just create a new Topic and filter it for that NPC. Topics get added to dialog when they are either said in conversation, or you can use an AddTopic in a script or the Dialog Results box.
(and yes, there are some Twin Lamps mod, but more are always welcome)

3: You can't create new soulgems, but you can imitate them with scripts. What you want can be done but you'll have to learn some moderate scripting. And it would be easy to make it specific to one weapon, then just switch out the empty gem with a full one. The full one would then have a script allowing you to heal yourself when equipped.

Hope that helps you get started, at least.

Thank you, Pluto! I am trying to do all my learning with tutorials and the good ol' trial and error but sometimes I have to ask. Appreciate the help!

I did kind of figure the soul gem thing was going to way out of my league. Oh well, maybe one day I'll be able to do more complex scripting. I'm hopeful! ^_^