I would say 33's and 4:88's would be more than enough and a 4'' lift.
That gear ratio is not recommended for 285s. Given that Dan has multiple Toyota's in various state of disrepair strewn all over his yard, I think this 80 may actually end up being a road tripp'n rig.
33“ – max. 3“lift – 4.56 - perfect for the trailer
35“ – 4“lift – 4.56 /4.88
37“ – 5“ or 6“ lift – 4.88
5.26 is to short
Stefan
33" and 4.56s is a good suggestion if Dan feels that his vehicle is struggling to get up the hills while towing a loaded AT. Truthfully, he ought to load the AT up to the gills and slap on a set of 285s (maybe borrow a set?) and tackle the hills around Reno/Tahoe to get a feel for the power band.
Given that this 80 is a junk yard salvage titled vehicle, I'd spend more energy on making sure the basics are covered and that the vehicle will actually travel a great distance w/o blowing up.
As has been suggested, although Dan isn't liking the suggestions, stay with 2.5". This is a great combo for overlanding w/o opening up Pandora's box of headaches and the wallet.
I'm trying to think is it even possible to drive from NM to Maine w/o touching pavement and I'm inclined to think that it is not. As soon as you pass WY, you start to hit private lands more and more and lots of private gates. So, realistically the remainder of the way will probably be on I-80 heading eastbound.
Good luck with what you decide. Your crew in Reno is giving you sage advice.