wow. those are some paint colors.

I'd fine some nice nickel hardware handles for your kitchen cabs. that will modernize those. Since that kitchen is surrounded in oak, here are some colors that go w/that tone of wood. And yes, if it was mine, I'd paint all of the baseboard (or replace w/taller, 4-5", white MDF baseboards,,,might be easier) at least in the downstairs/kitchen area. You may want to keep it upstairs.

will you be replacing the carpet w/the same type of wood that's in the kitchen? looks like red oak? if you do, have all of it stripped and stained in a soft, neutral brown. not dark,,,just nothing w/red in it.

as long as you're redoing the floors, get this new baseboard. that way you won't have to do quarter round molding when they install the wood floors against the old molding.

before and after wood trim

The way you state your questions makes me think you're going to sell this home once you update it. Or are you planning to live here yourself?

Definitely paint the wood trim.

Colleen,,,do you like more of a transitional updated look or more wood/country/1990's style?

do you happen to have a budget for all the updates? is it just cosmetic? any big items like a roof or HVAC?