If you drive it for 200k+ miles, you don't need to worry about trade value. Only if you buy a new truck every couple of years.You are right, Tacomas and Wranglers both hold their value like no other
I have a 2011 5.7 hemi Ram 1500, am around same age and don't plan on buying anything else. MY last Ram(not a hemi) had 200k+miles. Sold it to my brother in 2011 and he drove it and give to my niece and she runs the dog of it.
When they say RAM Tough, they mean it. Just my 2cents worth.