I bought my 2003 w/79k miles and performed the following maintenance (not including routine items like fluids, filters, shocks, tires, etc. ).
154,158 Lift pump (preventative) - GDP-391
154,158 Altenator support bracket (cracked) - Dodge part
158,400 Front brake disc pads - Performance Friction CM
205,351 PS reservoir o-ring - Pep Boys
232,100 Inner tie rod ends & stab links
241,056 APPS -MOPAR P/N 53031576AD
256,800 Lift pump GDP-391 (bad brush) - GDP warrantee
257,545 Fuel control actuator - Cummins P/N 4932457
264,300 Clutch, PP, Throwout, Pilot -Luk ProGold
288,837 Ball joints
297,909 RF wheel bearing hub
350,170 Inner/outer tie rods
350,170 Stabilizer bushings
372,051 Two injectors (#1 and #2)
382,106 Alternator
382,620 APPS
386,182 Injection pump
386,228 Injectors (3,4,5,6)
402,446 APPS
473,709 Water pump
474,263 Brake rotors, pads, rear calipers, rack & pinion, tierods, right front wheel bearing
492,579 APPS (Timbo special)
520,016 Fan clutch, fan clutch bearing
529,258 Rear universal joint
I also have a 95 and have had similar maintenance, but do not have a detailed list. But is shows that 3rd gen trucks will need maintenance also. I got out of the RV transporting business and decided to sell one of my trucks. I chose to keep my 95 for several reasons - fewer miles, cheaper maintenance, could get more out of my 03, really don't need a dually now. Biggest reason was that I just plain ol' like the 95 better.
As far as the OP taking a loss, sure he will take a loss, but he will take an even larger loss if he waits. The 06 will be depreciating faster than say a 97. All in all it just comes down to preference.