Thanks for the replies!
My Tacoma is a 4X4 TRD Sport DCLB w/ 3" suspension lift and I am running Cooper Discoverer STT Pros 265/70-17. It is a long bed so the wheelbase is a little long and it may be a limiting factor?? As for protection I have a Pelfreybilt Alum IFS skid plate, debating on equipping it with sliders before the trip. I will be honest and say I have never taken it on anything close to the terrain found in CO. I have ridden a dirt bike on off camber shelf roads and lived to tell about it. I purchased the book "Guide to Colorado Backroads & 4 Wheel Drive Trails" and was thinking of staying on the green (easy) trails for this trip. As for the Jeep, I don't know much about it, but will inquire. I do know it is a '92 Wrangler and more capable of the more difficult trails than my Tacoma. He is planning to trailer the Jeep out there. Looking forward to your suggestions and thank you!
You still have time to trade your truck in on a Wrangler. =) Poughkeepsie will probably be a bit much for you. I think you might be fine on the rest if you air down and take it slow. The guide book is a good place to start.
When you get there, start with the easy trails and work your way up. They have rental Jeeps too. They don't allow you to do Poughkeepsie or Black Bear. If you decide Black Bear and Imogene are too much for your rig, I would suggest taking a tour vehicle over one day. It is incredibly beautiful.
Especially your first time, its helpful to fall in line behind some other vehicles. It will help you get an idea of which lines to take. I did this almost every day. I only met one group on the trails there who wasn't friendly and helpful. They were locals, go figure. We were headed downhill when we met up with them. There was a wide spot in the road not 20' behind them but instead of backing up, they had us up back up about a quarter mile just because they had the right of way. I think that is the anomaly because it's hard not to be happy and in a good mood when you're in a place like that.