My 1996 cherokee country is leaking brake fluid on rear driver side. It's rusted pretty bad on the inside of the drum and on the back of the hub assembly.
what should i replace?

 

How about EVERYTHING??
If the drums are rusty, the cylinder is leaking, and I will bet the shoes are trashed, and the hardware is rusty too.............................................. Maybe start fresh with new everything??

OH!
And do both sides.

 

Will do
thank you

 

Also it won't shift when it should.
when I get it up to 3,000 rpm I have to tap on the gas pedal pretty good to get it to shift into second.
should I start with flushing the transmission and changing the filter.

 

No need to change the "screen" or to flush the trans. Just pull the drain plug, Let it drain. Reinstall plug and fill it up. Have 4 quarts of Dex/Merc fluid on hand.

 

I don't have any on hand but I can definitely go grab some.
thank you.
I'm just new to jeeps