We usually lean toward insulating the crawl space walls instead of the floor above. Sealing and insulating the walls is considered good practice in every climate, because it ties the crawl space to the rest of the house. Before insulation goes up, we close the gaps where air gets through, the same kind of air sealing services we do elsewhere in the house, so the insulation isn't fighting a draft.
Once the crawl space is closed in, it still needs a way to dry out. One of the most effective is a small supply of conditioned air from your heating and cooling system, so the space stays tempered like the rest of the house. We plan that air supply into the job from the start. If rooms above need more help, wall insulation follows the same order of work.
Fuel-burning appliances get checked first. Sealing a crawl space can, in some cases, make a furnace or water heater that vents naturally pull its exhaust back into the house. So before we seal anything, those appliances get looked at. If the check turns up a problem, I'll tell you plainly that the job isn't ready yet and what has to happen first.