Personally I'd grab the ED80 triplet in the classifieds at the moment, I think it is a cracking deal. I'd also like you to do so, as it would stop me from replacing my perfectly good ED80 doublet with it
If portability is key, an ED80 is a great starter scope, and you don't really outgrow it, just repurpose it. It can become a good imaging scope for DSOs later, or as a guide scope for a monster truck like a huge newtonian or SCT etc. if you go down that path later. In the meantime it is ultra portable and easy to use and will give lovely crisp views.
Almost any mount/tripod will handle the ED80 with ease, and they make a great base for something like the mallincam if you want to see the DSOs in colour. It will hold its resale value too, if you don't like it, you will easily get 80% of your money back on it.
Hell, if you don't like it *I'll* buy it from you in a couple of months for 80% of that price
There are so many ways you could go, I'd recommend joining one of the groups listed here and get to a viewing night and get your eyeballs on some scopes.