I know this house...
My second house, which is on my website was a 1740 saltbox colonian. Same issues.
I brought it up to date and improved the insulation.On that subject, you need to allow some extra room on the sloped rafters section for some prop-a-vent type of ventilation into the upper attic.This may mean building or furring down the rafters in this area to accept at least some insulation without touching the roof deck.I would use a rigid foam insulation in these areas, it works better and you can hold it off the roof deck with some strips of wood to create the air space.
This is an important area because it holds the most wieght of the ceiling joists.Hate to see this area become damaged.
So the house does not have a ridge beam i'm guessing?
Mortised at the top of the rafters with pegs?
If so I would give them a look and make sure everyone is tight.Then install the collar ties up towards the top to keep anyone from moving.Im' not to concerned about loads on the roof from wieght, more of a wind load thing to keep movement down.
Good luck on your project, been there got the T shirt.....