For my part, a good rider is a good rider, regardless of personality or how rich they or their families were/are. OK, in many cases, because of personal circumstances, some never have the opportunity to realise there full potential. I know of a couple of local riders to whom lack of finance brought a premature end to their careers, despite winning at club & national level. They were still quality riders though.
I was fortunate enough to have seen SMBH race both in the 60's on Singles, MV's and the Honda's (and even one time on a 125 EMC at Aintree). He was without doubt a brilliant rider, who could ride anything, anywhere, anytime.
He was just a natural. Despite having the advantage of coming from a wealthy background, he still had to ride the bike, no amount of money can replace natural talent.
As others have mentioned, it is impossible to compare different eras, but to me "Mike the Bike" is the greatest. I agree with Telbert about Jarno Saarinen, having watched him demolish a high quality field in the Mallory Race of the Year on a 350 Yamaha. It was truly a sad day when he lost his life at Monza.
We still have similar issues in our sport today. With the news that Casey Stoner is to return as a Ducati test rider, with perhaps the odd "Wildcard" ride thrown in. Already, the Rossi fans are complaining that "The Aussie Moaner is back".
To me, the fact that a top quality rider may return to MotoGP can only be a good thing, surely!
As I started this comment with, a good rider is a good rider, regardless of anything else (Personality included) This also applies to Luton's finest, who, despite all is still a great rider.
Merry Christmas & a Happy New Year to everyone