Most important things you need is Patience, Willingness to learn something different, An ability to search the internet for help...almost all the problems you will encounter have been solved already.
Linux is not windows, and if you have specific applications that do not have Linux euivalents that you are happy to use you should not change.
OK Plain vanilla Ubuntu is
1) Different significantly from Windows that you are used to
2) In a state of flux (lot of changes happening that may make you experience glitches)
3) But has the most comprehensive support and is the most widely used distro
4) It is intuitive but still a big culture shift.
Debian
1) Is stable...crashes are very rare
2) Things are tested thoroughly so unless you are on the unstable branch apps tend to be slightly out dated
Linux Mint is closest to your needs for Ubuntu and familiarity
Zorin OS as another poster has mentioned is alos good if you are person who would have difficulty changing from Windows like environments