So I've been cruising this form for a while. Ive always loved the E53 and I planned on buying an 01-03 4.4i about 5 years ago, but was turned off by vehicles that I could afford (high mileage, non-sports). As I reach the end of my college career, I feel as if it's time for me to look at something new. My current car now is an 2005 Subaru Forester XT w/ STI conversion, and out of warranty. I have had lots of issues, so far I've replaced engine among other things, at a whopping $6.5k and I feel as of the tranny is planning on taking a dump soon, so I feel I might as well cut my losses now and get out of the Subie as I'm out of warranty.
Now I've done my research...I'd be stupid not to.
I'm potentially looking at two different vehicles, that are from a BMW dealership and Lexus dealership. None are CPO, obviously.
#1- an '04 Kalahari Beige X5 4.4i with sport/19", premium, nav and all the bells and whistles except the cold weather package, which I think is sort of weird. But it has FULL (2-axle) air suspension, which makes me nervous. Has 60k miles and is priced at $17.5k.
#2 - an '06 Alpine White X5 4.4i with sport/19", premium. It doesn't have nav, but has an Alpine Nav unit installed, which makes me nervous, as it isn't the OEM nav, and gets rid of DSP and OBC. It also doesnt have cold weather pack, which sucks because I'm from WA and heated seats are nice, so are the headlamp washers

Has 72k and is priced at $18.5k
I plan on getting an extended warranty through USAA (Assurant), who I've used in the past . Now here's my dilemma. As I research more and more...the only
thing that makes me concerned is the transmission. A good friend of mine has had an '06 X5 4.4i since 2008, and all through college, it hasn't had any major issues, and still doesn't now. It was CPO though, and had 15k when she got it.
Is it really that bad if the vehicle has good maintenance? Subaru's have the same "bad" tranny issues, but it's always worse than it seems. My tranny, on the Forester, is probably going out after having 400hp for about 2 years now and is understandable. The trend I'm seeing on most car forums, is that they will only post issues that they've had, and those that don't have issues, keep driving and never post. All the issues seemed to get blown out of proportion, with several cars having the issue out of several thousands.
Is it getting blown out of proportion with the E53?
USAA offers three coverages which are more expensive for the 2006 due to mileage. Both plans are comprehensive, but don't include water leaks unless its a defective part. One is for 12 months/12k (2004=$2k, 2006=$3k), another for 24 months/24k (2004=$3185, 2006=$4k), and the last for 36 months/36k(2004=$4100, 2006=NA due to mileage).
Is it worth it to get the 36 month/36k over the 24 month/24k w/it being $1k more when thinking about the X5? I'm going to guess yes, but I don't know what the trend will be with yearly repairs.
Now with that being said, I've had a BMW before, my family loves them and parents both have them. I know about the little things that will pull your hair out. If I find the correct warranty option,
which vehicle do you think would be a better investment long-term wise?...considering mileage and year. The '06 is newer but has higher mileage, aftermarket alpine NAV, and higher prices for insurance. The '04 is less expensive with lower miles (great color), but is two years older, and has full air suspension which scares me.
Thanks for reading this lengthy post. And, I'm gonna beat someone to the punch and say, no I really don't want a Honda.