I am also in the process of starting to think about the possibility of maybe buying a new elctro-acoustic guitar. (I couch it in these terms in case my wife is listening)
To date, the best one I have tried is a Crafter Auditorium size electro-acoustic - great tone and at the upper end of your price range.
I tried a Fender but I hated the neck. I tried a Tanglewood but it felt too light to me.
I bought an Acoustic Guitar mag and that just confused me.
Knowing what kind of width neck you like helps a bit too.
You just have to try a lot of guitars and not rush into it.