If you had like Larry Holmes skills and Wladimir size. Would you rather want to fight against the likes of Bowe-Lewis-Holyfield. go through those wars for legacy and to test yourself. Or dominate guys like Chris Arreloa for easy paychecks. Would you want to go through the 'FAB Four' or just knock around mediocre guys for easy bank? There's advantages to both.
I would get bored in an utterly weak era, and a very tough era would be bad for my health (#healthcomesfirst - TMT) I'd settle for a somewhat easy era with a couple of very tough, career defining fights That way I could dedicate to other things besides boxing, like an acting or music career for example, while being a dominant boxing champion in my spare time. That'd be the epitome of G'ness
If i would be a HW with Ali“s Reflexes, Foremans Punch and Holmes Jab i would want to fight in this era. I would easily dominate the division, would make 1-2 Million a fight. The fight with David Haye would probably be my PPV breakthrough with all that trash talk on 24/7 etc.
Give me a weak era, but i'd have my last fight against a young hungry undefeated lion, dominate him, retire. Then the lion will go on to dominate the division, which just makes me look even better.