If you want a reliable car than the 535 is not the way to go. I am not saying some people have had reliable 535's but by in large it is one of the most unreliable cars to date for bmw, largely due to the HPFP which they STILL do NOT have a forsure fix for. They recently started using a different company to source these and are on version number 4 but no word on if this fixes the thing. I personally think its not the HPFP necessarily but the design of the thing. Also there are many other problems that happen including injectors going bad etc.

1000 bucks a year? ya right. One big repair will cost you 3k plus often times for these things. Even an electric water pump replacement or altnerator will be 1000 plus dollars for a dealer change.

I would go for an e46 M3 in that price range-a later date one as the earlier ones had problems. Anything after 2003. More power and fun with more reliability and less technology to fix.

I have a 530 and would never fathom getting a n54 tt engine. I am going for the e90 m3 now but the n54tt was shortly on my list in the 335is but as I read about it too much of a headache

 

There is a revolving door of E60's around here. I can't say hot or cold, but I'm thinking a bit higher than it should. Until I test a salesman with final numbers I won't know. There is a fantastic 550i with Sport and manual tranny that the dealer had listed for 46k, but immediately dropped it to 38k when I took a look.

I've been scouring autotrader, and have been to the BMW site a couple times. I'm finding the former site to be doing a good job of catching all the CPOs. . .

 

You can easily spend far more than $1000/year, especially if you let your stealer fix it. The auto transmission only can cost you close to $5K to repair once your warranty is up, and they are VERY unreliable on these E60. BTW check Carfax for the car, if it went through car auctions most likely its mileage was rolled back.
Even under warranty is not always possible to fix some problems since you need to convince your dealer that you have a problem and BMW dealers are one of the worst in car industry to deal with especially when they see a potentially expensive repair like transmission.
I have heard and seen on forums many stories about E60s dying on the road due to electrical problems. The batteries also like to exit suddenly on these cars if you let your car seat in your garage for 2-3 days. So yes a show-stopper is very much possible.