If you don't have cruise control in your TJ, go ahead and check out the guide Chris has on installing it. Long trips without cruise control are a pain in the ass. Outside of that, you have a hard top and tires that aren't too aggressive, so you won't have as much wind/tire noise as many other TJs out there, so it should make a good trip for you and your pops.
I have cruise control luckily. Yea the TJ I have is a pretty quiet ride. Quieter than I expected. As for your other points I agree. The great thing about 90/00's Jeep's and other cars is that they still have a lot of the simplicity of older vehicles and much of the convenience of modern without going overboard. And there is a great nostalgia of having manual windows