IMO Medellín, Colombia (known as "the city of eternal spring") is about perfect from a weather perspective. It averages around 23c year round (varying between about 18 and 28). It does have a rainy season, but even then mornings are often sunny (afternoon not so much).
Direct quote from my gf who lived in MVD for a while - “it’s cold and rainy often, and in winter it sucks because none of the houses have central heating”. For context we now live in Central Europe (toasty summers and long cold winters).
She loved being there and to be honest I'd definitely visit, but I guess there's more to it than just the average temperature outside
Great points. Thank you. Perhaps my friend's perspective is tempered by his being native to Seattle. He mentioned that he thought Montevideo was the southern hemisphere match to Seattle. Hmm.