New owner with sudden remorse

[Retroman1969]

I have two '99 Boxsters, and a 2000 Jeep Wrangler. So far the Boxsters have been more reliable.
My daily driver is the Tiptronic Boxster with 130,000 miles on it. Everything works on it perfectly and it runs it's butt off every day in all kinds of weather. $8,000 total invested in it so far. The other is a a 5-speed with 98,000 miles and is literally like new.
All three vehicles have needed normal wear parts replaced, but that should be expected in a 15 year old vehicle.
My Indy Porsche mechanic has been in business for over 20 years, and says he has only seen 3 engine failures in M96's. One from an IMS, one from ignoring a coolant leak and being allowed to severely overheat. (can't remember the 3rd).
If I ever want to replace the IMS (with the updated improved one) and RMS my quotes have been: $1300 with the manual and $1600 with the Tiptronic.
The Jeep has stranded me 3times in the past 6 months, required nearly $3000 in repairs/maintenance, and is now sitting in my garage with a blown head gasket and cracked head (which I've read are extremely common on them, unless you get the 2003-2006 with revised head, but those are well known to have oil pump failures).
So I say drive and enjoy!