The which do you prefer aspect makes this more interesting, as a number of these are more subjective.
Climate: I really strongly prefer SF. It is in a general sense of comfort year-round, cool, but for my tastes, not too cold. Very nearly can't be beaten, and I think objectively people agree the California coast has one of the nicer climates in the world.
Education (includes higher education): So, as someone holding 2 degrees from UCF, I don't have bad things to say about the school, and there are good educational options in Orlando overall. However, SF, esp. Greater SF, has truly world class options for all levels of education, reflective of the fact it is a global knowledge magnet. It might be a Top 5 metro on the PLANET for that (joining LA, Boston, London and Hong Kong)
Dining out: SF has more options overall being a more diverse and larger area. However, I think there are plenty of options in an Orlando sized city too-so honestly this one isn't that big a deal to me, and Orlando does have certain advantages, including the Caribbean, Southern Cooking/BBQ, and Price Point.
Cultural offerings: SF by a dramatic margin. I don't think SF is necessarily Top 5 in the US in that regard, but considering the wider region, and old and new institutions that are there, it is most certainly Top 10. Orlando's cultural options are not to the level of other major Florida cities, reflective of a place that was effectively a town up until Disney came to the area in the 60s.
Classical music performances: I would have to think SF, by a dramatic margin. Orlando has an Orchestra, but SF has one that has won 16 Grammy's, an Emmy, and a Pulitzer Prize. It is on the cusp of being a modern day "Big 5" orchestra within the US. Then you have the San Francisco Opera, also Top 5 in US, maybe Top 10 in world, playing in a venerable old building which I believe is the oldest in the US, where the UN was founded. I don't believe Orlando even has an official opera company at this point though I could be wrong on that.
History: Even something like this can technically be subjective. And one could argue that both Walt Disney World and Kennedy Space Center have played tremendous roles in our history, from Greater Orlando. But I mean... the SF Bay Area has 13 NPS Historical Units... and the city of San Francisco has 18 National Historic Landmarks by itself. This really isn't a fair fight in some categories.
Healthcare: I've never heard particularly bad things about AdventHealth... but Stanford Hospital is ranked 12th nationally..and UCSF Medical Center is ranked 7th... so objectively it almost certainly comes out ahead.
Diversity: I guess this one sorta depends on what you are talking about since diversity can mean so many different things. SF has more foreign-born population, and at the metro level it is 26% Asian (leading the US perhaps?) and 22% Hispanic... but then Orlando is 31% Hispanic and 16% African American at the metro level.. and actually even 4% Asian I think is more comparatively than a number of comparably sized Sun Belt metros, so it's reasonably diverse too, even though SF is much more multinational. I think the argument for Orlando here could be perhaps an increased diversity of thought and lifestyle compared to SF which is more unilaterally urban cultured and liberal? Not sure-I tend to think this one also goes in SFs direction, but I think there is at least some case to be made for Orlando here unlike some others.
Entertainment: I guess that depends too-as far as family entertainment-Orlando very well might win, as it is a global destination for that sort of thing, given the theme parks.. however SF is larger and generally will feel much more vibrant as a city overall and in other kinds of entertainment-so to answer this question fully you have to determine how "entertainment" is being defined (diversity and quantity of offerings vs. a hyper-focus/hub status on amusement park based entertainment).
Nightlife: I really haven't experienced SF Nightlife so I can't comment-it is a much bigger area so I would tend to think it would have more options-but at the same time I don't think it's known for nightlife in the way Las Vegas, Miami, or even New York are. Orlando-I will say that is perhaps one of the most underrated nightlife scenes of any city in the US-since it is not a polycentric city and Downtown Orlando along Orange Ave (which gets closed off on evening weekends) is the primary nightlife hub for the city.. and with the nearby presence of UCF, things get quite active.. truly. I would say that the area on Orange Ave between Church Street and Wall Street and extending onto those almost perhaps calls to mind a small scale version of 6th Street in Austin-I have generally said non-Disney parts of Orlando feel a decent bit like Austin-and I think would be very surprising to those that have not previously experienced it.
Public transport: San Francisco perhaps isn't as great as it could be or as some of the best cities in the US, though it is still arguably Top 5 overall, and runs away from Orlando here.
Strength of local economy: Umm... Orlando. Of course. lol.
Scenery: SF for me-I can see why people would make the case for Orlando-but I like the dramatic topography, world's deepest natural harbor, redwoods, decent size mountains, vineyards and ocean surrounding SF.
Cost of living: San Francisco. No question.
Shopping: San Francisco likely has more high-end options than Orlando-but this one is actually somewhat competitive given the presence of mall culture in Orlando, the quality of the outlets-etc. Put it this way-Orlando mall shopping might be one of the best in the US for deal-finding. That said, SF does have the larger retail base... but Orlando still has more retail options than someone like me could ever want.
More friendly people: This one is truly subjective and honestly there are friendly people everywhere IMO.
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