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Posting up in here as I have a good friend who has a 2000 528i also, and he is right around 410,000 miles today. Still on original auto transmission (had to top off fluid and change filter due to sluggish shifts, but that was IT). I will toss some advice in here and you can use it as you may...
The oil filter housing gasket it literally a $6-10 part. That job is right near the top right of the engine, and you must remove some items that are in the way like power steering reservoir leaned to the side, vanos oil line, etc, but it is not a bad job. While you are doing that you can easily replace the vanos oil line and crush washers as it's right there and you'll be disconnecting it anyways. That should save you **GASP* $917 minus the cost of the gasket and vanos oil line which will come in around $40ish I think.
Front shocks, mounts and hardware can get expensive as there are a lot of parts to replace, but from my friend's experience doing this, the entire coil over can be removed from the car without compressing the spring I believe. If you were to purchase everything you need and pre-assemble it off the car so it's ready to go, that entire job should not be too bad at all and is simply removing the old strut assembly and installing the new. Should be able to get the entire front shock assembly both sides for around $400-500ish I think. Front sway bar links while you are at it are pretty simple to do and right in your face while doing the shocks, so knock that one out at the same time. They are cheap as well, lemforders probably $20-30 each maybe?
Brake lines - don't even try that on your own, that is definitely something to pay for. However, it says "Rubber brake lines" which means it's not the hard metal lines that are bad, it's just the rubber ones that connect from the hard line to the caliper. That too is a pretty easy job, and if you have a friend that can help bleed the brakes, you can save yourself gobs there. I think those lines are around $30-40 each maybe.
Now the oil pan gasket is a beast of a job, at least on the E46 I did it on which has a very similar set up to the E39 528. In order to even get at that pan gasket, and to remove the pan, the entire engine has to be supported from above with an engine brace ($99 at harbor freight) and then the steering rack and lower control arms removed and dropped down to give you clearance to get the pan out. This job took me an entire day, was a TON and TON of work, but the parts were not bad, I think I spent around $99 for a bunch of replacement bolts and the oil pan gasket. Get OE BMW if you are going to attempt this simply because you never want to touch that again. Now, that being said, how much oil is it leaking? I made the mistake once of power washing my wife's so i could see how much it was leaking and I think the pressure from the power washer pushed a small chunk of gasket out and then it started to dump one quart every 3 days!!!! now that is a BAD leak. So get under there, hand wipe it clean and then inspect over a week or so, also constantly check your oil level. The gasket on my E46 330i was leaking for at least 10 years, but it was a very minor slow leak and adding oil here and there is certainly a hell of a lot easier than dealing with that job. So assess and inspect, and also ENSURE the leak is coming from the oil pan, as any other oil leak INCLUDING THE OIL FILTER HOUSING GASKET can manifest itself on the oil pan bottom since that is the lowest part of the engine. This is why cleaning it all good can help trace the actual source of the leak.
AC no leaks evident, but $325? MY GOD WHAT RAPAGE.
All in all, these are all jobs you can do yourself, you just need time, and the right tools and sometimes an extra set of hands. THAT CAR WILL LAST 400K MILES EASY. So 5 years if you did all this is an underestimate. But I'm not sure what other service history your car has, so there may be other jobs to do as well. You need to look at it as a whole and determine if it's worth it for you to put in the work, time, money and effort, or dump it and get something newer. But I will say this - they don't make them like that car anymore. That car was BUILT to last. And that M52 engine is far more bullet proof as well as leak proof compared to the M54.
New (old): 2003 E39 M5 TiAG
Old: 2001 E46 330i Steel-Grey Metallic (Totalled)