Yes, most definitely use CHRIP to program it. It is technically possible to program them through the front panel of the radio, but don't even bother. Skip the Chinese software.
See if you can get a CHRIP file for the Baofeng from a local ham and just upload it to your radio, that would be the easiest way to get started. Otherwise, try to get a list of local repeaters and an idea of which are the most active. Last option is to check out repeaterbook or radioreference and download whatever repeaters they have (they don't always have all of them). CHIRP also has the option to download by city or county or something, but again they don't have everything.
Amateur licensing goes Technician > General > Extra in that order. You have to pass one before you can test for the next highest. If you decide to, you can pass all tests in 1 sitting and go from "zero to extra" in 1 day for the same test fee (if any).
The Technician license is all you need to do everything that your new radio will do, but most here recommend at least testing to General, and in the same test session if possible. The Tech test is stupid easy (ask about the 8 y/o kids that aced it), and there is a TON of overlap of the information for the General exam. General opens you up to the good stuff (HF) if you decide you ever want to, for minimally more effort.
Find a local club and go say 'hello', they'll tell you what you need to know to get started.