Paint the trim after it is installed, then paint the ceiling. Sure, you can paint the crown before they hang it but the filler used in the nail holes and the caulk needs to be painted anyway so painting it prior to install will only save a small amount of time, it any. Trim, ceilings, walls is the correct order.

You may get more advice in the decorating forum. I would not lower the crown. Your ceilings are not high enough for that. Any neutral for the walls, and I would paint the crown, ceiling and any trim 1 or 2 shades lighter of that same neutral, but not a stark white. As for lighting, how involved do you want it to be? Hiring electricians? Cutting holes and running wires? Good luck!

I agree and so does DH, the shed looks best. Thanks to robo for the mock up! Eld6161, my boys' room has one small porthole-style octogon window. I think it's because my second floor probably originally had only two very large bedrooms upstairs. At some point, a previous owner added a wall between one if the rooms to make a third bedroom upstairs. As a result my DD's room on the back dormer has two big windows and no windows in the front room which is the boys.

You know... that wood looks pretty good. 70s still had half-way decent wood. So, ok I get that the modern palette has moved away from brown as the neutral to grays. However wood stain color choices have evolved the same way - plenty of grays now, from charcoals to silvery bleached out grays. Not to mention the dark ebonies, jet black, grayed out browns etc. Weathered gray is a popular color. What I dont get is the automatic default to WHITE 99.9% of the time on this forum. PLEASE consider sanding/staining this wood instead of encasing it in an opaque plastic film. Having lived with "landlord white" throughout the 80s -90s, white painted trim looks good for about 5 mins before it starts getting dinged and dirty. In a lot of settings, I think dark trim of whatever color just looks classier too. There are various products out there - rather than a full-on stripping job (yuck) you might consider some of the heavier bodied stains that just need a light sanding to give it some "tooth" (removing only clear finish without going deeper and removing the color.) I dont want to write a novel so Ill just leave it at that - the woodworker forum could give you m ore specifics..