I'm making plans to contract significant repairs and renovations to my 1927 Sears Craftsman house, which was last updated in the 1960s. I can only afford to do it in stages, over five years or so, so is there a sensible order in which to tackle the major systems? Some of the projects will be: updated electrical; 2nd story bathroom (only one bath now, on main floor (there's no plumbing except radiators on 2nd story); new boiler or maybe central heat/air; plaster repair; insulation; new shed dormer roof; new kitchen cabinets and countertops; and refinished floor.

I guess I need to get to the dormer roof first, and I'd like to put in the 2nd story bath next.

But does tackling the 2nd story bath open a can of worms? Such as being forced to address whole house plumbing and electrical if these systems are too outdated and worn? Kind of like you can't fix a portion of something that's broken, you have to fix the entire system.

How hard is it to install central heat/ac in an old house with plaster walls? Will the plaster be destroyed throughout?

Is it a good idea for me to walk through my entire house with an independent appraiser to identify potential problems up front?