need advice on Rolex for my dad

[WatchGuy1337]

I was hoping you guys and gals could help us (mcl/Marie and I) with a decision we've been trying to make regarding a gift for my dad.

My dad turns 60 soon, and we'd like to get him a second Rolex to mark the occasion (so he isn't without when his current one goes in for service!). Several years ago, my mom bought him a TT DJ with Jubilee bracelet and silver dial. We would like to get him a sport model, but are not sure which. There are a million factors we've considered, but I think it boils down to these:

1. it needs to be something HE will enjoy wearing. He's not a watch enthusiast, so he won't get a kick out of wearing, say, a Sub LV just because it is "unique", collectible, etc. It needs to have aesthetic appeal. He will appreciate a unique piece a little, but the aesthetics really do trump. He will be wearing it in both casual situations and also with a shirt and tie (for work).

2. (much lower concern) one day, this will likely become one of my watches, so something I'd appreciate having is preferred (but much lower priority than #1). I currently have a black bezel GMT II, and I'm sure I'll be lucky enough to get some other models I have my eye on well before I inherit my dad's watch.

edit to add: 3. must have a date

edit to add: 4. prefer to buy new, but would consider pre-owned under the right circumstances

Some of the models we are considering include:

1. Sub LV (the "old" one, green bezel only) -- nice piece, unique, collectible, I'd love to have one; concern: will the green be a turn off for him or be less versatile as far as when he could wear it?

2. Sub 16610 -- timeless, classic, imho it's the most versatile of the sports models as far as dressing up/down, every family should have a "basic" sub; downside: not very different than my GMT II

3. Deep Sea -- unique, a statement watch for sure, I'd like to have one; concern: it's very heavy and bulky, and might not see as much wrist time as a result

4. TT Sub with blue face -- looks great, I really like it; concerns: it'd be a second TT watch, and it's very copied (by Invicta, etc.)

5. SS GMT II ceramic -- would "match" mine, one day I'd have 2 generations of the same watch, very functional (although he doesn't travel much), similar versatility as the sub; concern: has the more "blingy" bezel design, would be a duplicate in my stable one day

6. anything else someone recommends

So, this has been a long post...I'd certainly appreciate hearing your thoughts!