That's a tough call, actually.

I haven't had my La Valentina for 1.5 years now, and since then I have just had a La Pavoni Pro. I use a naked portafilter and tend to overdose into a "large" Elektra basket that will take 15 grams or so. So I still tend to make a heavy ristretto on my current machine, albeit much smaller. The characteristics are a little similar, but rarely do they have the body or intensity of the triples I would pull on Valentina with the LM 21 gram basket.
I've actually got 2 58 mm triple baskets at the moment, the 21 gram LM and the Synesso ridgeless 18 gram. I am just waiting on UPS to deliver my Vetrano at this point. My plan is to start using the Synesso basket and see what it's like. I am kind of hoping to taper my heavy caffeine intake. I like at least 2 drinks a day when I have time, and triples add up a lot faster than doubles....

I know what you mean about the chocolate flavor of the coffee vs. the syrup, or even melted dark chocolate. My gateway to coffee was (gasp!) white chocolate mochas. I used to love them, and hate coffee straight. Over time I made my mochas with less and less syrup until I stopped altogether. A few months later I decided to make a mocha and poured it down the sink pretty fast. It tastes revolting once you can pull a good shot! I felt like I had buried all the depth and interestingness of my coffee underneath a shallow, at once fake flavor that overwhelmed everything.