Tell us your interests and then we can advise better on places. Think about this question. What kinds of things do you like, and where are some great places for those things? For example: diving, Roman architecture, hiking/trekking, Italian food, bustling markets...
Personally, I stay almost exclusively in hostels, when I'm not Couchsurfing.
Rough figure of how much you took?
This wouldn't be a fair answer - it depends on where you go and what you do.
Wing it.
Travel light -- I'm on month 17 with a 30l rucksack. More mobility and security.