Excellent advice everyone. Thanks for all the tips and the links you shared, greatly appreciated!
I have 30 days, which I can stretch to 45 days (max) if need be, for this trip. I am still undecided on whether I should take a shot gun approach to this trip, which is to see as much of Europe as my time frame will permit and then perhaps identify key cities I might wish to come back to later for a more Zen-like experience. Or, as Holly suggested, target specific cities to spend some time in activities I enjoy doing. I like music (opera, symphony, British pop/rock bands), museums and art galleries. Basically, I like places with tons of history.
I have been to Europe (Barcelona, Frankfurt and London) in three separate occasions within the last 10 years and because my trips were work-related (5-day meetings at the most), I did not have the time to enjoy the places I visited. I've been contemplating on doing this trip for the past few years but it's only now that I am forcing myself to do it. I told myself that if I don't do it now, I'll procrastinate again and again and end up doing it about 25 to 30 years from now, upon my retirement. I'd be alone on this trip, although I have a friend who might later decide to join.
Hostels, B&B and Europass (and travelling at night) are probably the ones I'd look into for now. The freeloader/servas/couchsurfing thing is attractive too. I like the idea of interacting with friendly people who are interested in hosting someone from other countries; plus, the perks of being able to save money. I understand that some time and preparation is required to ensure pleasant experience with these arrangements.
Speaking of hostels, are Slovakian hostels as bad as they are portrayed in the movie "Hostel"?
One thing I did not get from any of you was how you handled your money. I know you have to bring lots of it but can anyone tell me how you kept your money safe. Do you have loads of CAD or USD tucked in your socks or underwear? Where did you buy your pounds and Euros? I have USD and CAD credit and debit cards. Will these be safe to use in Europe or am I better off paying cash all the time? Did you feel safe walking the streets of Milan or Rome with cash and passport in your wallet?