1. look for visible cracks or plaster/patching marks especially on the columns and beams.
2. if have the budget, might as well do it now especially if there's nothing done to the roof since the house was built. just paint the house to give it a fresh coat of paint. move into a "new" house must look new. :P
3. exterior painting is subjective. some houses I see have never been painted in ages so you see peeling paint, etc. the paint is there to provide a layer of water proofing to the house as plaster/bricks/concrete is porous. but exterior painting is a big cost for landed house since need to erect scaffoldings. I would say about 10 years once or when see peeling paint happening whichever comes first
4. can't escape pests. they can come over from your neighbour's house unless your house is surrounded by a moat. just try to keep your house clean so they won't stay and have parties.
contractor/builder are same actually.
for option A, a contractor/builder can do everything under his contract. some works could be subcontracted out by him eg: electrical, carpentry and fabrication of windows. your floor to ceiling window most likely need a PE to be involved due to safety issues.
for option B, you need to engage a PE as you are touching the stairs which is a structural element. unless you meant hacking down the walls next to the stairs then may not need if it's just brick walls and not columns or RC wall
both options are considered A&A just that B is a major A&A since there's more work to be done