Well, there are many ways to look into this, and a lot of it is quite subjective, so in the end it's very much a personal choice.
Regarding the 300SE: Though it looks the same as the W111 Coupes, it is technically a very different car. The M189 engine is the cousin of the one you find in the 300SL, But with an aluminum block. The air suspension also provides for a unique ride. The 300SE is technically much more refined than a 250 or a 280. That doesn't mean faster. But a different personality, a different sound and a different driving experience. One must be receptive to it though. Go on the M-100 Group forum. People there know these cars well as they share their suspension with the 600 and the 6.3. They will be of good advice. Also, before you take a decision, I would strongly recommend that you drive both a 300SE and a 280SE. That would be the best way for you to decide which one you like most. If, after driving it, you don't feel the 300SE is a special car, then don't buy one. The additional complication won't be justified for you.
As per a 250 Cabrio vs a 280 Coupe: I've owned several coupes and of course I've looked into buying a Cabrio. But something always held me back from doing it. I find the Coupe to be the most elegant of any Mercedes of that Era. Less so for the Cabrio. With the top down, the Cabrio looks like a big barge with a cushion on the trunk. I only like it's look with the top up, which does not make much sense for a Cabrio. And even with the top up, it is not as classy as the Coupe. My problem was solved when I realized that for the price of a Cabrio, I could own both a Pagoda and a Coupe. The Pagoda was designed as a convertible from the start, and it looks good with the top down. Not like the Cabrio which seems to have come as an after thought.
You already own a Pagoda, so a Coupe may be a good complement. A 3.5 would also be a different experience, as the 280's engine is very close the the one you have in your Pagoda. Again, driving one and compare would be the best way for you decide.
As per values, I think the Coupes will go up. I think they have been under valued. They have started going up already, so now would be the time to buy one.