Denny Swift

I think it depends on whether you are more interested in driving or showing off. If you're more interested in driving for the pure pleasure of driving, the answer is obvious. If you're more interested in a vehicle that will get the most attention and be the star at C&C and shows, then get the RS.

Adrift

lol Wow, someone is threatened. That gem of a response is pure pablum, and sounds like an excuse for not having something others do. The car doesn't dictate what is done with it...the owner does.

GTS is obviously THE performance deal of the bunch x1000. Manual trans, reasonable comfort while still plenty capable for hard road carving. Easily a great DD and a canyon/ track warrior, if desired. The value of the MT experience alone is paramount for many people...but only you can decide the relative value of that.

The SRS is an entirely other creature.

First, it's a convertible. Do you want a convertible? I wouldn't have it any other way myself, but many aren't as captivated by that. YMMV
Second, it's an RS, meaning comfort and practicality (and heaps of $$$) are sacrificed for performance / experience. It's loud with an insanely impractical roof, and will be a lot bouncier on sub-perfect roads than the GTS.
Third is no MT. I am a MT die hard, so this one is super difficult for me. But this is so personal...I am hoping the lightning fast downshifts making the noises the SRS does will adequately replace the engagement of the MT. We'll see.
Fourth is that gt3 4L. One of the better NA engines made today. The GTS 4L is nice and is certainly no slouch, but the gt3 4L is in another class entirely, not to mention the sounds it makes.
Fifth is the music the intakes make. My ring tone is now a recording of those intakes during downshifts. I've never heard anything like it. I CAN'T WAIT!
Sixth is it is a totally different price range. Paying upwards of $200k (assuming no ADM) is a LOT more than $100k. $200k is seriously fat wallet territory. $100k is something most reasonably successful people can reach with a little effort.
Seventh is totally subjective, but that the spyder is a gorgeous car, like ferrari gorgeous. The cayman is ... a reasonable looking coupe. YMMV
And oh yeah...the SRS will be rare / special / blah blah.

So...is it worth 2x+ the price? The answer is both "absolutely f'ing not!!!!" and "i can always push retirement off another 5 years to get the srs..." IMO only those with lots of excess cash, or those who are the hardest of the hard cores, should get an SRS. For that very small sub-section of the population, it makes perfect sense. For the rest...not. An idiosyncratic plus for me personally is how threatened it will make (most of) the 911 folks feel. lol I love forcing point-bys from people in more expensive cars, but especially 911s. And the fact it is the ultimate (ICE) boxster incarnation means a lot to some of us.

Eh...what would I do with all that free time in retirement anyway...

Lucifer

Actually, the Spyder\GT4 is the performance deal of the bunch. Before purchasing mine I did a lot of research (maybe too much) and I found out (by analyzing dozens of 981 GTS&Spyder deals) that on average a 981 Spyder brought 25% more money for similar MSRP and mileage, while being objectively the worse car (if we ignore looks, which is subjective). This was what basically made me go for a Spyder instead of a GTS. It is just the better deal all around.

No idea how the GT4RS or the SRS will depreciate, will have to wait and see, but I don't think they will do too well, just because of how ridiculously expensive they are for what they offer.

Adrift

They'll be burying me in my SRS. (unless those bastiches release a MT version at the last minute)

Drifting

Similar to adrift, I don’t plan to ever sell my SRS.

I think the GT4RS/Spyder RS will do just fine with depreciation, and will hold its value far better than a GTS. All RS models do.

And the 4RS/SRS represent the final ultimate Pinnacle of the NA Boxster/Cayman. All future ones will be electric. That plus hello a real Motorsport engine, insane sound, and for the Spyder RS, a look that truly rivals a convertible Ferrari, I think the value of my SRS will be just fine. And if not, it doesn’t matter as I will never sell my incoming Spyder RS.

The only thing that remains to be seen is how well a manual (not PDK) GT4/Spyder will hold its value relative to a PDK only SRS/GT4RS.

If the 911 GT3 world is any indication, I think both the manual spyder/GT4s and top dog (but PDK) 4RS/SRS models will all hold their value quite well.

Adrift

That I don't intent to sell it (while I'm still breathing) is also what will let me put miles on it without wringing my hands (incl track). If the SRS is a stretch for you at all, and you might sell it, fear of mileage can be a very real thing. Then you become the kind of owner Denny was describing.

Leonel

im taking the SRS
I really enjoy driving the manual gts 4.0 but the SRS is special