That is a very broad and very long request.....
Take it from someone who hears things differently than most.
You need to research the story of the Jazz era and decide what you want to listen too.
Todays world is lost and does not understand, or care, how we got to where we are today
musically. It has always been the same story. From Scott Joplin to Dr Dre.
It is all about self expression.
So, what SELF do you want to listen to
Watch the Ken Burns Series on Jazz.
Watch the 1988 film Bird produced by Clint Eastwood.
It has always been the same story. Musicians expressing themselves. Musicians dying much youner than they should due to drug, alcohol, and most notably to me SOCIAL ABUSE, due to race and class.
I know your question is simply, how do you find what you enjoy? It is more what timeframe do you relate to:
Ragtime of 1910s Scott Joplin
Fox Trot of 1930s Hot Lips Paige, Fletcher Henerson Chu Berry Illinois Jacquet. Listen to a tune called Mutton Leg by Count Basie
Swing of the 1940s Ellington, Basie, Woody Herman and the thundering herd
BeeBop of the 1950s Charlie Parker, Dizzie Gillespie, Monk
Cool Jazz of the 1960s Miles Davis, Coletrane,
Avante Garde/Hard Bop of the 70s Lew Tabackin Phill Woods
Rediscovering the Heritage of the 1980s Wynton and Branfrod Marsalis And all that encompasses them
DEATH of Jazz due to Kenny G and the smooth jazz push of the 1990s.
Kenny G, Candi Dolfer,
There are no jazz channels on the radio anymore.
So I plug my cell phone into the radio input button, turn on you tube, Pick a jazz tune and let the sounds randomly come across. Thats the best advice this 56 year old jazz player has for the novice.
Hopefully this will spark others to say something. If not, my point is made.
RIP self expression.