So I would consider myself in a bit of a pinch from the standpoint of maintenance requirements on these old birds so will throw in my 2 cents. Since I have plenty of penny's :-)
1) To buy a new plane with similar performance of my 680FP you would be over 1 million dollars. On this new airplane you would have all new gear but anyone owning a new plane can tell you they break plenty and the costs to repair are generally up there pretty high. Lets just drop any conversation about engines because old or new they all have to be replaced at some point and the costs are equally distributed.
2). I purchased my 680FP for around $70k knowing up front it was going to take a bit of work to get everything fixed and going. I screwed up and put it in one of the worst shops in the country and spent another $40k screwing around and wasting time.
3) I then flew the plane to my shop where it has spent another 3 months of me working with my mechanics here to get everything done in TN fixed properly. We ended up having to literally go through everything those guys touched and redo it plus other things that they didn't even find. Another new starter, new hydraulic pump, rebuilt master cylinder, totally rebuild brakes due to shop totally screwing everything up. Point is, I've had almost 9 months of solid work getting things fixed.
I've now flown the plane a total of about 12 hours and about to put another 6 on her this weekend. So far I've had not a single drop of skydrol on the floor (KNOCK HEAVILY ON WOOD HERE!!) and everything is performing awesome. I've also added a new engine monitor, G530W and redone most of the panel.
I don't have a glass panel because I don't want one, prefer the steam gauges.
So lets jump to the high side of the purchase and say I spent another $60k plus my original $70k for a total of $130k on the plane. I have a plane that carries 7 people, baggage, is pressurized, storm scope, all the instruments I need to fly in most any kind of weather, Deice and so on. It also fly's readily off a 2900' grass strip and looks awesome in my hanger.
So 1) plan on spending whatever money you need to in order to replace everything broken and don't skimp. Find a good mechanic and get the work done right the first time. What you will end up with is a plane that will go the distance for you and have most likely the same number of problems or less than the brand new airplane you purchased.
2) Forget the engine replacement costs, new airplanes need new engines as well. If you get 500 hours on yours before you have to replace one then you're 500 hours ahead of the guy in the new plane.
3) Annual costs are going to be similar and. Your new airplane may end up with an AD you didn't even see coming (since its new and hasn't been battle tested yet). So just forget about it.
In the end it all comes down to whether you love your bird and enjoy flying it. It is not cheap to own any airplane and if you buy a plane thinking it is an investment or that you'll get your money back out of it or even that it is more economical to own than to rent, well, you're a fool. We buy airplanes and fly the pants off of them because we can and it's cool. That is it.
I am very lucky because I own a software company and need to fly the country doing training. It would almost always be cheaper to fly the airline, but it is never as easy, quick and pleasant. So while it costs more to fly my own plane than to fly commercially, the ability to hop in the plane this morning and be at a customer site this morning or this afternoon on a minutes notice changes everything.
But the point is, the why you fly isn't as important as the whether you can afford to. If you can, and you want your own plane, I see absolutely no benefit to spending the extra million dollars to be spending money on the same things in the end. Don't get me wrong, if I had the money I'd throw it on out there just to say I have a new bird, but at the end of the day, I'd rather spend a whole lot less money getting my bird impressive as hell. So when I show up and people go, "WOW", I can say yeah, she's a 63 model and I did that. :-)
Glenn