And in many respects being a Roman nobleman before the bloodiest of the late Republic civil wars seems to have been better than being a 19th century peasant or a Middle Ages king. (And the time referred to in
Western history as the "Middle Ages" saw some relatively great times for some rulers outside Europe.) So it does always depend on what the specific trade-offs are, which is basically what
@FedericoFCavada and many others here have said if not in so many words.
Questions like these are great thought experiments. But at the end of the day, would "I" like to live in another time and place? is not something "I", a product of
this time and place, cannot honestly answer.
The genie (closer to the mythological Trickster than the fairy godparent who has your best interests at heart) gives you a choice:
(a) go back to whatever point in your life you want and try again - without your current accumulated knowledge or
(b) take your current accumulated knowledge back
to a different life
Meaning what you
really want to do, go back and fix your mistakes, is impossible either way. You don't know how or if the knowledge you "now" have even applies to your "new" situation. Which would you choose?