I probably wouldn't consider an older BMW in that price range if maintenance costs/reliability are a concern. Unless you don't mind doing the work yourself. I've never owned a BMW so I can't comment on actual experience, only what I hear/read.
I have a cousin who lives in Michigan who owned SRT Charger until it went down an embankment one snowy night. He mostly loved the car with the exception of having to drive it during the winter (rear-wheel drive). He replaced it with an all-wheel drive R/T Charger and still loves it and never mentioned anything other than maintenance being needed. I should note, however, that part of my family has employment ties to the auto industry and their thoughts on American cars are probably biased. I guess my only comment on a Charger would be to get an AWD model. Reviews here show a mixed bag as far as reliability goes - looks like it is dependent on the model year.
I don't think you meant to say you're interested in driving "boring" cars. If you did, you should definitely consider other makes/models. Maybe an AWD Infiniti G? There should be plenty in your price range. I've owned Infiniti in the past and found it to be enjoyable and relatively trouble free.