[one]

My answers in blue.

Do you want to stay with a 250cc bike?
no, i was thinking larger for the performance, long ride ability with a passenger, weight.

Do you want to stay with the cruiser style bike?
yes

Do you ride long distances?
long? up to 125 miles + a day

Do you carry cargo as in camping equipment?
cargo is important. not so much getting to the location but more so on the ride home. storage is always nice, i found it difficult to run to a store and take something home without it being held on me personally or under the seat.

Are after market third party accessories important to you?
windshield, saddle bags moreso then luggage to keep weight lower, i am in the NE so heated handle grips and seat is always a plus.

Is performance and handling important?
yes