I currently have:
1987 Mercedes 300SDL-purchased several years ago and I have rebuilt the suspension, replaced most of the damaged interior parts with good used one, etc. But, I think the head gasket is leaking and the transmission has stuck in one gear and has worked after I changed the fluid but there was a lot of clutch material in the pan and I think it's in need of replacement. Fixing the head gasket and replacing the transmission is likely to coat ~$4k and take way too much time to be worth it.
2000 Porsche Boxster - just recently bought it, it needs a starter (which I knew when I bought it) and a thermostat (which I didn't know) but seems ok otherwise. I thought it would be a good fun car and allow me to try autocross but I don't think trying to daily drive a boxster would end well and I don't like it as much as I thought I would. I bought it a month ago and other than driving it once to get it smogged it has just sat in my garage while I try to forget that it's there.
1996 Subaru Legacy Outback - very high miles (491k) but most of the drivetrain and suspension have been replaced with new or lower mileage parts. The issues are that it is on the 3rd used transmission I have tried in the last couple years and this one is already starting to leak and the second gear syncro is failing. Also, there is a loud metallic pop from the front suspension and I have checked over everything and can't find the problem, and most of the parts are new or nearly new, and I have decided that it's not safe to drive and I have put enough effort into trying to figure it out that I don't think fixing it is going to happen.
I think I would like a new Ford Bronco base model/7 speed (if I test drive one and actually like it), but that's not likely to be feasible for another 1.5 years with the way production seems to be going.
Other than that, I can drive the Mercedes to work for as long as it keeps running, all the stuff that would be dangerous if it broke is in good shape (suspension, brakes, flex discs, etc) so i could just pull over and call AAA if something happens. The part I am frustrated with is none of these cars are reliable enough to really use for anything anymore. I have a bunch of vacation hours and made plans to drive the Subaru and do a bunch of stuff this summer/fall but now I'm looking at canceling all of it until I can get rid of some or all of the cars I have and get a replacement.
I would like to be able to drive on dirt two track roads (which the Subaru could do fine), go on a several hundred mile road trip, drive up a steep grade when it's 100 degrees, etc. If I sell the other 3 cars I would have ~$10k I could spend on one or more cars to replace them, and one Boxster sized parking space and two S class Mercedes sized spaces if needed. Or up to ~$30k to spend on a new car, but I would rather not buy a new car without at least driving a new bronco first.
Any suggestions? I'm not entirely sure what I should do but looking for ideas. I am not happy with the situation I am in now, so I want to take steps to change it as soon as possible.