His damage output is pretty good, and I even got him a purple 2 hander that has a chance to generate 2 guard on hit, but he still dies too quickly. I've maxed out reaver and manually activate ring of pain myself because the ai just drains his stamina. What skills/gear can I get to help keep him up longer? Reaver is the only specialization I've found tough to get the hang of so far.
What!? Why would you spec him like a tank? 
You reduce damage by aggro management.
War Cry gives you aggro. If you must have guard, use Unbowed.
Are you using him as a Tank? If so, I'm not really into that. He's nice as DPS, though.
Get turn the blade and turn the bolt from Shield Tree and craft him tier 3 armor with tier 3 materials.
Presto, now dragon rage is more of a threat to you then dragons.
Nah, strictly as dps, although it is difficult for cassandra and even blackwall to hold aggro with him dpsing away. My main(a dual-wield tempest rogue) has options to slip away and survive in combat, bull's reaver is having a harder time. I also suck at using parry and slash, shield block, properly lol. What about combat roll? Evasion? Those kinds of skills worth investing into?
My PC is a SnB Tank that is mostly controlled by the AI, so all my companion warriors are 2H's.
Combat Roll is one of those things that I've learned to live without. This is a good thing, since I put priority on putting points into TIB's specialization. If your problem is aggro management, I'd look into positioning and see what your other 2 party members are doing. If your problem is reading enemy tells (or, this is your first playthrough and you're getting used to the fights), then Combat Roll is a life saver.
Block and Slash is fantastic, since it also blocks the kicks from a dragon. The way I play him is purely single target, though, and especially when using Dragon Rage, stuff dies really quickly.
There's nothing wrong with using Unbowed (War Cry without the taunt), in the sense that if you take Charging Bull, it's only two points away. If you upgrade CB, it basically becomes a 0 stamina ability, since your next Mighty Blow (50 stamina) won't cost any.
That said, Blackwall hasn't got any points into his specialization yet, so I went into Battlemaster with him. There's something deeply satisfying about pulling something and then smashing them into the ground.
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