And as I'm a bag lady myself, here's what I've found --
Peppers -- compact hots (habanero, ghosts) are perfectly happy in either a three of five gallon bag. Slightly larger ones (jalapeño, pepperoncini, Aji Limon) do better in a five gallon.
Dwarf tomatoes -- if you keep on top of watering and fertilizing, they do great in a five gallon bag. Last year I put one in a 10 gallon (ran out of fives) and really didn't see any difference in plant size or production. I also stuck it's sibling in a three gallon bag and while it didn't grow as large, I still got a decent yield from it.
Tomatoes -- last year I had Moravsky Div, San Marzano Nano/Bush and Early Wonder Pink in 10 gallon bags (again, I forgot to order more fives). The year before I had an EWP in a five gallon bag. The one in the ten gallon did grow a bit larger and produced more, but I think ten gallons was overkill. I'm guessing seven gallons and one plant would be ideal.
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