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Keep in mind that if it's winter, Europe will be cold. More so in the north obviously. Not sure what climate you're used to, but places like Germany and the Netherlands are definitely cold. Southern Spain, Portugal, Italy less so, obviously, but they still can be chillly and rainy. I've read that Greece can be quite stormy in winter as well. Parts of the U.K. can be reasonably mild in winter I think, not sure about Ireland, but expect rain, for sure.
I don't know how to interpret having an "income" of $2500. Is that the total amount for the trip? If so, I'd count on keeping that other $5K available. Europe is not cheap, although it can be done fairly reasonably if you're careful.
I also think it would be great to base yourself in a few places for extended stays. I'm thinking of doing a month in Lisbon next fall, with side-trips by train or perhaps car, but otherwise just getting a feel for living there. Probably not the best choice of city for someone who can't walk much, however, since Lisbon is very, very hilly. So you should look carefully at any city you consider in that light.
Wherever you go, it sounds like a great adventure!
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