The biggest challenge you face is that all of the vehicles that seem to interest you appear to be made by Chrysler, a manufacturer whose future is anything but certain. There's a reason why Chrysler is in such difficult financial straits; they've not invested in developing quality vehicles and their popularity and resale values have suffered accordingly. This is not on the basis of individual vehicles, mind you, but the entire Chrysler/Dodge/Jeep brand.
You also seem to be highly influenced by factors completely external to the vehicle itself. Why or how does who may find the 300 to be most popular affect its suitability for your purposes? Even so, the 300 is a dated vehicle platform that includes many "luxury" features cobbled together cheaply. The best aspect of the vehicle is its Mercedes-developed vehicle frame which Chrysler has pretty-much wasted by stacking it with cheap components. It's like building a shack on a piece of prime real estate. Chrysler tried to overcome this by putting a big HEMI engine under the hood of the 300C, but all that accomplished was to create a faster poor quality vehicle. The reason why you see so many "gangstas" driving 300's are because they have absolutely no relative resale value and used ones can be bought so cheaply, something that's only going to get worse when the platform is redesigned for 2011-2012 and anything appealing about the older generation models will no longer be current. The 300 is the luxury car of last resort.
The Avenger is a reasonable full-sized sedan whose most notable feature is how unremarkable it happens to be. There's absolutely nothing distinctive about the Avenger and it suffers from the plight of every Chrysler vehicle, spotty reliability and cheap feeling low-quality interior materials. It will certainly carry you from A to B, but you're likely to spend a great deal of time wishing you were being carried in a nicer vehicle and wondering why you've received so little for your money.
The Jeep Patriot and Compass are underpowered half-heated "slot fillers" designed more by Chrysler's accountants than its engineers whose only potentially-redeeming aspects would be four wheel drive. Poorly-appointed compared to the Grand Cherokee and other Jeep products, the most attractive aspect of either vehicle is the low price for which a used example can be had.
The Pacifica "crossover" (a.k.a. station wagon) has suffered sales decreases every period for the past few years, and the reason is fairly obvious; as competitors have improved the quality of their product and introduced new and compelling models that reflect advances in technology and consumer preferences, Chrysler has continued to shuffle the same old deck of cards thinking a gimmick here or doo-dad there can substitute for actual improvement. The Pacifica's lackluster characteristics are made worse by the fact that it also happens to be one of the most unreliable vehicles in its class.
Common to all of these vehicles are the abysmal resale values that reflect the failings of both the vehicles and the entire brands themselves. FIAT is 2-3 years away from offering any kind of substantive improvements. While Ford began their turnaround some 3 years ago (under their own steam, without needing the more than $60B Chrysler and GM pick-pocketed from our grandchildren's piggy banks), Chrysler's ownership invested very little in research and development and there was simply no new product "in the pipe" to bring to market anytime soon. Furthermore, there should be very little compelling about supporting a company who was rewarded for failing while Ford, the only American manufacturer with a right to exist, has been penalized by the burden of having to pay their own bills and compete with government-sponsored competitors with bottomless wallets.
Even so, Ford continues to produce better, more compelling, and more reliable vehicles than either Chrysler or GM while improving reliability to meet and exceed the most respected Asian competitors. What does it say that Ford revolutionized its own company without a dime of government assistance while Chrysler and GM haven't done as well or as much after receiving some $60B, enough money to not only make terrific cars, but cure cancer and return America to the moon? While GM and Chrysler were spending billions trying to advertise their same old lackluster product, Ford was quietly and simply building better vehicles. There's only one American manufacturer you (and every American) should be supporting, and it's neither Chrysler or GM.
Furthermore, Ford has FAR superior vehicles in each of the categories you mention. The 2010 Ford Fusion is the Motor Trend Car of the Year and a full generation ahead of the Avenger, and Taurus, MKS, Flex, and Escape are all miles ahead of any Chrysler counterpart. Finally, as a wife and mother, Ford's industry-best safety should be the most important feature of all.
Best of luck. I hope this helps.
