A month ago I was traveling back from out of state, I had the cruse control on at 70ish and started going up a hill. Part the way up something weird happened... almost like the cruse control stopped working. I pulled over and checked but couldn't find anything wrong.

4-5 days ago I keep getting some weird slip, almost like tires broke free, every time I took off from a dead stop. It happened 4-5 times but didnt happen next time I drove.

Today I was driving on the freeway and every time it would downshift out of overdrive the tranny would slip a little (could see the rpm's jump a bar or two and could feel the power loss) before hooking up. And now the issue with the start from dead start has shown its head again.

I am over due for a tranny fluid change but was recommended by a friend to hold off an drive it till it fails. What do you guys think?

Any advise would be good for me as I am broke too. :/

 

Auto transmissions can have some black magic associated with fluid changes. If you change it religiously you're good to go, but it may start slipping depending on how it's driven; a fluid change might help. If on the other hand it's way overdue and starts slipping, a flush might finish it off...

Sounds to me like you'd better start saving up for a used transmission, this one might be on its way out. You can inspect your fluid, but I'm with your friend in not changing it until you have a better picture of what you're dealing with.