i say start with the large tank. SOMEDAY, in a few years probably, i want to get probably a 100 gallon tank and keep one or two oscars in it, maybe a couple other fish if i can. rather than starting off with a 50 or something, i'd rather just save up, jump for the 100 right from the start. i think my plan will end up with...
a 200 gallon with some bala sharks for my husband
a 100 gallon with a couple oscars
a 20 gallon with a pair of red honey gouramis and tetras
a 10 gallon with a divider and 2 bettas