Things to consider based on your questions:
On the tranny dipstick, either bend a lazy "Z" in it or cut about 3/8" off the tip end and it will solve the problem of it popping out!
Transmission shudder, service transmission (filters & only ATF+4 fluid) and then bring level above full mark by adding an extra 1/2 to 1 qt. of fluid.
If that does not fix problem, try adding some Lucas Transmission additive to fluid.
These transmissions like having extra fluid in them and seem to work better when slightly overfilled.
Install a ProVent filter! See this thread to understand why they need one! >
viewtopic.php?f=5&t=80491It will keep the oil out of your hoses, CAC (intercooler), and intake.
Do you know when the timing belt was last replaced?
Is the EGR system been blocked off or removed? If not, it needs to be done ASAP!
Thermostat; if it is leaking, you should replace it! DO NOT use a Crown Part, they are junk.
CAT, remove it, and put a straight piece of pipe in its place. Replace muffler with a straight through type like a Flowmaster. Engine will run better without the junk CAT and restrictive factory muffler. If you need part numbers for muffler, just ask.
Tunes: Some like the FREE DIY tunes, and some like to pay for the GDE tune. It's your call.
Lots of good advice on this forum! IF you need help, just ask...
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Supporting Vendor and Moderator of LOST05 Jeep Liberty CRD Limited
Ironman Springs/Bilstein/Shocks
Yeti StgIV Hot Tune
Week's BatteryTray
No FCV/EGR
Samcos/ProVent
SunCoast/Transgo
Carter Intank-pmp
2mic.Sec.Fuel Filter
Flowmaster/NO CAT
V6Airbox/noVH
GM11 Bld.fan/HDClutch
IronrockArms/wwdieselMount98 Dodge Cummins 24 Valve