Em The cup holder is very useful. I had two, one for me and one for ds.
The travel systems do cost a lot but if you're going to walk millions of miles then it's good to get the right one. If you're tall then it's especially useful to look at whether you will be able to stand straight up and use your full stride length. When I was at your stage there wasn't one that allowed that. I think the twin Bugaboo that has now come out probably accommodates a longer stride length then the chameleon though.
I walked about 6 hours a day with ds until he was about 2, and still lots after that. If you have very lively infant, then going for walks is a very good way to keep them entertained, and get them to sleep too.
People who take buses generally prefer an umbrella fold one or the bugaboo bee, but I was never a bus person. An awful lot of the decision is unique to your lifestyle unfortunately, so following other people doesn't work so well.
I always liked the Emmaljunga ones, but in the end I got the chameleon. It's very handy to be able to turn the handle round so the pushchair can put pushed up to a table in a cafe, just as if it was a highchair. It's at just the right height. We even used it at the piano so ds could sit in the pushchair and play. It's at the right height for that too.
Blah, blah, blah. Sorry, I could talk about this all day.