Can you tell me about living in Key West as a young person?

I am a 22-year-old college graduate. I have settled myself somewhere for summers, but I am thinking about what to do November-April.

I worked as a street performer this summer, and I did very well. It seems that the crowds I got during the summer would be the kind of people who go to Key West in the winters. I have never been to Key West but I’m having a little fantasy about it for this winter. Can people who know it well please answer some questions for me?

1. Are there lots of street performers? Is there space to perform? If you’re one who has worked in KW please get in touch.
2. How is real estate? Easy to find an apartment/sublet or a room to rent for a few months? How much will I have to spent?
3. Are jobs very competitive? Reckon any restaurants or whatever will be hiring in the winter?
4. How big is the town? Walkable? Bikeable? (In terms of one side to the other).
5. Lastly, does anyone know any kind residents who know anyone looking for a subletter or tenant or babysitter or anything for the winter?

Thanks a lot! I probably won’t make it anywhere until January. Any information is very helpful.