That is a heck of a transition, from a relatively light and well balanced chassis to a somewhat ponderous in comparison borderline sports car/grand tourer. Curious to see how you think they compare because you have been quite spoiled by the S2000. My GT car experience was with an R129 and while it was great having a very comfortable but somewhat still sporty car I just wished it wasn't so slow.
In the last decade or so I've owned an E-Class (2001 E430), 4c, 166, GT-R (2017), CX-5, Levante, Evora S, Stelvio, Guiletta, Smart For Two, XKR (5.0), and soon the Vantage. It was either that or an F-Type R (2014 5.0 RWD version), and I think the F-Type still has plenty to fall in value, and the rust issues caused by India being India are unforgivable.
Most of them were just to scratch an itch, or have something for a winter beater (Smart) in the snow, the only one I kept coming back to was the S2000; I just wish it had a bit more power. I've driven supercharged S2k's, but I didn't like them, mostly because they look too Fast and Furious and mine is bone stock and will always be. I've driven a number of Astons when I was looking around and the 4.3 is a nice upgrade to the S2K; yes one is a heavy lump and the chassis isn't a patch on the Honda, but the 4.3 has a nice 'you need to rev the shit out of it to get the most from it' feel that the S2K does. The 4.7 kinda lost that feeling.
And yes, I have an abusive relationship with Alfas. I really want to like them, really! They look the mutts nuts, but there's not a single one I've driven or owned that I would say is a good car to drive from a petrolhead point of view. The 4C Spyder broke me somewhere...a lightweight carbon fibre tub, minimalistic with a driver focus, then they put an engine that could set off car alarms in the morning which was fun, but had the rev limit of a fucking diesel, and a horrible automated manual tranny. Oh and the seats were agony after a couple of hours driving. It should have been the Elise of Alfas, but god they fucked it.