So... some background on my preferences.
I'm not a red wine drinker - the tannins aren't to my liking. I enjoy tasting them for comparison purposes, but I can't recall ever finishing an entire glass of red wine.
I'm also not really a white wine drinker because they're generally too dry for me. I've had a few Rieslings - particularly the sweeter grade German wines - that I have enjoyed, but those are rare as well.
I do enjoy dessert wines as long as they're not too syrupy. Trockenbeerenausleses and Beerenausleses (the two sweetest grades of German white wines) are among my favorites.
My favorite Port so far is a 1977 Porto Rocha Colheita. But the 20-yr old Quinta do Bom Retiro from Ramos Pinto is right up there. The Rocha is, to me, exceptionally smooth and well integrated which I find appealing. The Ramos Pinto has bolder - perhaps rounder? richer? - flavors. I might eventually switch to it as my favorite, but since I've only had it once (and that was in Portugal sitting on a terrace on a stunningly beautiful afternoon, so my opinion of it might be slightly biased

I have tasted a few rubies and can tell the difference between various house styles, but I'm not yet capable of describing those differences to others. Which makes it difficult to describe what I think I might like.
So... I'm reasonably certain that the softer the tannins the better. I tend to prefer fruitier flavors, but not to the point where they're smacking you in the face (or becoming "grapey"). And I also seem to like wines and Ports that others describe as "mellow" or "smooth." Which in my brief experience seems to come with age.
All that being said, what would you recommend? I suppose you'll need a price range, so let's try to keep it under $100 for a bottle. (Recommendations over that price are welcome, though, as I'll keep them for future reference!)