Answer: Zone 8 is iffy for even the hardiest of citrus, so your idea of planting in containers and overwintering indoors is a good one. I'd choose dwarf varieties so they will remain a more manageable size throughout their lives. Here are a few recommendations:
Meyer's Lemon: bears large, sweet lemons almost year round.
Dwarf Bearss Seedless Lime: large fruits ripen in winter and early spring, established plants can be everbearing.
Minneola Tangelo: a grapefruit and tangerine cross, winter through spring ripening fruit.
Kaffir Lime: leaves and zest are used in Thai recipes, very fragrant leaves and unusual fruit.
Owari Satsuma Mandarin Orange: seedless, juicy fruit produced in winter and early spring, hardiest of all the mandarins.
All should produce fruit on an annual basis.
You can root the top of a pineapple and have it grow into an attractive plant, but it probably won't produce edible fruit. If it does, the fruit will be quite small - mostly skin and core. But, it might be worth a try!
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