Well, I dont think I can stomach a summer in Houston driving my Jeep w/o AC, so I was looking around for a good deal on a truck. I found a nice '06 Tacoma with a TON of options. Is there anything that I should look for with this model year? Does anyone have any info on how these tow? (I will need to pull my Jeep [~4000lbs] on a heavy trailer[~1000lbs]).
That '06 Tacoma probably costs a mint, and from my research it isn't able to tow what you want.
Why not just spend the money (less money actually) that you would spend on the Tacoma to retrofit AC into your Jeep.
Depending on how old your Jeep is, you may be able to get an OEM AC retrofit kit from your local Chrysler/Dodge/Jeep dealer.
I see many advantages to the Tacoma, (more creature comforts, etc), but if it won't tow your Jeep and trailer, then it doesn't seem like the vehicle for you.
I assume you use your Jeep for off-roading or 4-wheeling and that you may not want AC on it, but AC isn't a big loss on the drivetrain when it isn't on and it really doesn't add that much weight.
That is my .02