Everything you say is correct. And it would mean you also have to LIFT the bike as you move the bike forward. I can no longer even GET my '08 on the centerstand as of this summer. Just barely last year. Which adds all kinds of worries for me all of which require too many words to explain so I just won't.
I'm a few years younger than you are, sir, but I too find it difficult to accept that I can no longer do what I was able to do when I was twenty-one. I can just about handle the weight of my C5 Classic EFI. In my humble opinion, 195kg/430lbs is too heavy for a five-hundred single, especially when you remember that the iron-barrel Bullets weighed in at 163kg/360lbs.
As you imply, just getting the bike onto its stand can be hard work. Retracting the stand and lowering the bike down on to its wheels can be even harder, as we know from reading all the comments here. Many new motorcycles today are no longer fitted with centre stands. Maybe the reason for this has something to do with the enormous weight of modern machines. We are all getting older, but at the same time all the bikes are getting heavier!
It could be that the centre stand on your 2008 (EFI?) has developed some play in the pivot, possibly the two holes in the frame are elongated. This would result in a sloppy stand which goes way over centre and allows the rear wheel to sit on the ground. This could be the problem experienced by Geezer in the original question. If this is the case, it will be extremely hard to retract the stand, as it simply wants to slide forwards.
I have found that if the stand goes just over centre when it is deployed, so that it is a few degrees from the vertical, the bike will simply roll off with a fairly gentle push forwards. No heavy lifting required.
So, if the stand pivot is worn, I guess the only solution is to eliminate the excessive play, possibly by welding the elongated spindle holes in the frame and/or new parts.
I bought a new C5 EFI Euro IV model last year, and the first job I carried out was to modify the centre stand to prevent the pivot pin, or spindle, rotating in its mounting holes in the frame and wearing them out. I may not keep the bike long enough to judge whether the modification actually works, but I wasn't happy with the stock design and could foresee possible problems ahead.
I will try to post some pictures later.