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Off hand, the Chrysler 300 is lacking in the reliability department while the Lexus will come with higher repair cost.
The two cars could scarcely be more different from one another. What is your interest in each?
What year models of the two are you considering and what is your price range?
Well, I am not "married" to either of them. Navigation is a must. There is a good possibility the car will be handed down to my 23 year old son. that being said, I don't want a "mom car". I am certainly open to any and all suggestions you could offer. Like is said reliability and maintenance cost would be a big variable for both of us. Safety would be a big factor for me is he is going to get it.
I would scratch the 300 off the list. They are having problems ranging from 10,000 mile tire life and bad wheel bearings to generally bad finish quality.
The Lexus is a very nice car and has had no significant problems commonly arise.
The maintenance is not overly expensive (less than a BMW or Mercedes to be sure). The only down side is that when something does break, it will be expensive simply because of the brand.
The other benefit of the Lexus is resale value. Lexus is one of the best brands for holding value, Chrysler is one of the worst.
Another good value in a luxury car similar to the Lexus is an Infiniti M class. The price point tends to be a few thousand less than a Lexus with the same mileage and age.
A general rule of thumb these days is to stay away from American made vehicles. The quality has really suffered as the companies tried to stay in the black. It is improving, but I would wait a few years before jumping back on the American made bandwagon. Sad, but true.
German and Swedish cars are still of generally high quality, but the maintenance and repair costs are prohibitive.
Japanese cars are, as expected, very reliable and tend to be affordable to repair when compared to their European counterparts.
The Korean manufacturer, Hyundai, has come a long way. The Genesis model in particular is changing the luxury sedan market and getting high marks consistently.
If you have any more specific questions, I would be happy to offer my opinion. I try to stay abreast of the car market, both new and used and genuinely enjoy the process of comparing relative value by employing my experience with each brand.
Feel free to reply to this post if I can be of further assistance.