Dilema: keep Jeep or trade?

I do love my 2004 Liberty 4x4 for the most part, but am getting tired of the "kick in the rear" on periodic shifts in and out of first gear.  One dealer said this is just a Liberty "quirk" and another said they couldn't diagnose without a warning light on or recreating the noise (it happens only periodically, but is unnerving when it does).  Another dealer offered to talk it over with their top tech (will go there again on Thurs).  In the meantime, near-by Dodge dealer has leftover NEW '07 Caliber with AWD and basically "make offer."  It has the CVT-II transmission and the AWD automatically engages traction to the wheels that are able to grab, unlike the Jeep's system (on-demand 4WD) where I understand the grip only one wheel at a time in front or something equally goofy... (?).  The rest of the equation is that I live in Florida... where flood waters, hurricanes, and an occasional emergency trip to PA in the winter warrants good traction and the ability to get through the weather issues.  The Liberty sits up high... is "trail rated" for water fording, and nearly paid off.  The Caliber gets better mileage (this would be my daily driver/work car), has AWD traction, but is lower than the Jeep, yet has more safety devices (ABS, Curtain air bags) and would lower my insurance since it also comes with an alarm.  I hate to take on payments for another 5 years, but then I don't know IF the problem on the Jeep can be fixed and afraid in the meantime the Caliber will be sold... so what's a person to do?????  What would YOU do in my shoes?  (By the way, the shoes are Reeboks bought on sale and fit well).  Hope this didn't give anyone a migrane!  THANKS!  

i'd keep the jeep. drain out the old fluid and replace the filter. if it only happens in 1st, you might need to get the bands adjusted. a transmission shop will have a better idea then the dealership. if you go to a tranny shop, and it's fixed, be sure to stop by the dealership and show them the work order and start asking questions.  
I work to support my Jeep

IMHO, i'd get the jeep fixed. if it isnt paid off yet you'll automatically be upside down on a new car loan, if they sell the caliber then they sell it. wasnt met to be, but you need to get out of debt rather go deeper into it. i'm sort of in the same situation, my 2001 jeep cherokee 177k miles transmission was slipping, so my mechanic said he would swap out mine for a used 45k mile tranny for 800 bucks. i still owe 4k on it yet. so this all means i'm paying 4800 on a beat up jeep that i get to worry if it will at last at least till i can pay it off. plus, another way to look at it is, say you go and make deal with the stealer on the caliber, say you get it for 16k, they will add in the amount left from your jeep. not knowing how much you owe, we'll just say 4k left on the jeep. that takes the caliber up to 20k, plus the bank might not even give you a loan on something that msrp is only 16k but you'll be needing a loan for about 20k, plus all that interest(free money to the bank) and your paying for a jeep that you dont own anymore. trust me i wrestled with the same situation, been losing sleep for the last week over my jeep. hope this helped... but this is all i got told too.  

Thanks for your replies.  I owe about $2700 on the Jeep and I think I will test drive the Caliber just to see how I like it.  If I do, then I will first see if Jeep can be repaired under warranty and effectively and hold it.  If this route doesn't work, I will just try to pay it off sooner, then look for a deal on a Caliber AWD.  You're right, MYDOGTJ, going upside down isn't smart unless there is no other choice.  Fortunately, I can often use my old '90 Miata for work and running around and let the Jeep "rest."