The CIS is the limiting factor in your build list. I'd use a hotter cam (GE60) and go with carbs if you don't have to worry about emissions. Look to Arron Burnham @ Rennsport for a distributor and get two MSD boxes to fire it. 46 PMOs are a good choice and 10.5 : 1 with twin plug is fine on 93 octane pump gas (total timing about 28 degrees). I would look around for a rebuild-able set of '78 or '79 heads and leave them stock (other than springs, retainers, guides and a good valve job).
Winter starting is really no big deal. Carbs have accelerator pumps; a few pumps of the go pedal, turn the key and fire it off. It may take a little while to get used to the protocol. This set-up is good for 250+ hp and could be tuned for close to 300. You will like this motor.