I need an old school D&D master to help me

I've played 2e DnD for ever as that was the preferred edition of my group of friends. There are a lot of kits, but or DM always shied away from them. He preferred to run the basic classes, and that worked for us very well.

The thing to keep in mind with 2nd is that your characters perform specific narrow roles. You aren't Rambo or Heman. If you are a thief, you are a thief. If you are an illusionist, you are an illusionist. You're not going to be Raistlin or Drizzt. The kits are where you start being those types of characters, and that's why a lot of DMs didn't allow kits. They were just over powered for the most part.

Also, the games differ a lot based on your DM's play style. My DM was in to a lot of role play and minimal combat.

If this is your first time playing 2nd ed, I suggest a fighter or thief. Keep it simple.

2nd Ed is a lot of fun. Ravenloft is a great campaign.

Here comes the heretic:

Play Pathfinder.

It is D&D 3.5 + a lot of minor improvements. It has a tool (Hero Lab) that knows the rules for you. You can stick to Core rules, or go all in and munchkin yourself up with all the additions. Everything is available online, so you can also play the game at no cost, or look up things real easy with Google (d20pfsrd.com and paizo.com are your friends).

D&D was bought by Hasbro, who made them dump their “Open Source” (Open GL) approach, and with 400 employees could not compete against Paizo with 40 employees, as well as made Wizards make a version (4E) that shares fate with a Highlander movie that would have come between Highlander 1 and Highlander 3. Everything Hashbro/Wizards do is about reigning in IP again, to support those kinds of business models. Paizo has disrupted that, in their alternative approach. It is not about making money on the rules, it is about making money on the stories. The value add from Hasbro/Wizards is no longer significant nor competitive.

5E is fine(ish), but why go for shackles when you can have freedom? . Paizo is making the next version of Pathfinder, have made Starfinder, and is collaborating with the makers of Hero Lab to go cloud. There is also a cute retro Pathfinder game coming out soon (Kingmaker), in the style of Icewind Dale 2 etc.

3.5 is where it is at. unless you go BECMI which is still fantastic as long you pretend hollow world never happened.

check out this wonder. what a great time to be alive when you can download the grand duchy of karameikos for 5 bucks. 'murica!

A creative GM can make game play interesting to say the least ... once had a GM and flipped the tables a little bit and had players roll almost all Drow characters and his entire campaign was our rolled characters versus other Drow, creatures and critters in the Underdark, and against traditional "adventurers".
It was a shameless steal of the players being members of Bregan D'aerthe but a lot of fun. Oh and we stuck to 2nd Edition rule set for the most part.

Actually I like 2nd edition BECAUSE it is not loaded down with rules and you can make some things up on the fly. True I used some third party rules critical hits from Dragon magazine I believe and the jousting rules from Chivalry and Sorcery but 2nd edition felt very clean to me. Couple years ago I went out and bought all the pathfinder rulebooks... turns out there was a lot because they didn't keep bringing out new editions... now they are bringing out a new edition. Still found it far too complicated.

We tried to go back for a few sessions, 2e is unplayable now, feels like windows 3.1

I would say go with 1e, but that includes Unearthed Arcana (to get the info on Barbarian, that is). That is what I play (obviously with GM interpretations...we are in their world now...wait, I don't think I can say that). I never really liked the idea of the Cavalier, but meh...I played a lot of Wizardry, Bard's Tale and Might and Magic 1 and 2 on the PC. Also played pnp (pen and paper) Rolemaster (you want a detailed game, this...this is detailed...obnoxiously so). We incorporate Fumbles, Criticals, etc. Just grab the DMG, PHB, MM1 and 2, FF and UA and you are set to go!