I own a 2008 access cab and contemplated selling it to get a TRD double cab to build up. My friend talked me out of it with a couple of good points. First, the number of times I would carry extra people is very slim. The wife and child can fit in the truck no problem, so that's good. Future kids are an issue but a bridge to cross when we get there since I would rarely take the entire family on a truly off-the-grid trip. Second, with the long bed, since I'm less than 6' tall, I can sleep comfortably in the bed with a sleeping platform. This is HUGE considering I'm in the northwest where rain and winds are the norm and sleeping on the ground in a tent is no fun. And not having a roof top tent is one less thing to worry about. Finally, my friend convinced me buying the TRD edition is useless since I'm going to rip out the suspension and put my own and can install an air locker - he's right. Why pay the TRD premium if I'm ripping it out to put in my own stuff? Taking my regular SR5 and building it up is just fine.
As far as building up your 1995, I see nothing wrong with that either. You will find that the dimensions of a newer Tacoma is larger than your existing one. So I would be pretty inclined to keep your truck. There are also tons of aftermarket parts since the number of those trucks sold is huge. Lift kit, tires, air locker, bumper + winch and you're set, probably for around $5K, less if you can find good used deals. The only caveat is if your truck is in need of an overhaul on the engine + drivetrain components. If that's the case, the economics start getting questionable based on the amount of work to do.
In the end, I say stick with the access cab. Do NOT get the double cab + long bed because it's just too long - unless you love the sound of metal scraping on every piece of earth or rock you traverse. I would also cast my vote for keeping the 1995 and building it up. You always have notes for a future build and it probably would be very easy to sell the truck if you did decide you wanted a new one.