I have purchased mostly used cars most of my longish life and repaired them as required, including a few engine rebuilds or crate motor replacements, rebuilding automatic transmissions, etc. and have spent many hours at the drag strips with cars I built, all of this with seldom having concrete to work on or a garage to work in. I have even blueprinted my own motors, as much as one can do at a home shop.
I grew up in the muscle car area as a teenager and lived that life to its fullest for many of my years. However, while I really enjoyed that era, those cars and trucks can't compare to vehicles of today in terms of safety, build quality, reliability, handling, fuel mileage, power or anything else germane I can think of. I remember those days fondly, but will never own another vehicle of that era out of choice. The only positive attribute for me of those autos over today's autos is those earlier generation autos were easy to work on and had so much room to do so, while today's are nigh impossible for the home mechanic. Easy repairability was a good thing as their life span was relatively short and so was their reliability.
I drive all of my vehicles for many years and rarely purchase new or semi-new, so depreciation is never a concern. My new Ram 2500 diesel 4x4 is most likely the last vehicle I will purchase and I expect no major maintenance problems during its life span with me, which is important at this stage of my life and a primary reason I purchased new. Was it expensive? Oh, absolutely. But at this stage in my life it was worth it for the peace of mind and long-term reliability I expect to have.
I purchased a new tractor two years ago to clear my densely forested retirement property that has heavy clay soil and layers of rocks- many very large that required a tractor and grapple to move. I purchased new as I needed the reliability to complete this task whenever my employer decided it was okay for me to work on my own things. And now it is completed and the tractor and implements have paid for themselves while working very hard and providing supreme reliability when used at their maximum capabilities. A farmer friend of mine still has to work on his old Ford's on a regular basis just to do regular grounds maintenance around his place and there is no way his equipment would have completed my tasks in the time frame I needed. My stuff needs to work hard when I need them to and old and worn out does not work for me anymore.
So for all of you guys who want to purchase old vehicles and want to spend the labor to keep them going and are content with the reliability on long trips with your loved ones and the potential lack of safety should that vehicle be involved in a serious accident- good for you. I am no longer in that group. Oh, BTW, I no longer repair dishwashers, clothes washers, clothes dryers, coffee makers, home electronics, etc. But I do my own tractor preventive maintenance, modifications and troubleshooting as prior tier 4 tractors are still relatively easy to work on.