I don't like them but a windscreen will help in the comfort area.
Also yours and your ladys butt will thank you for a Corbin saddle.
With luggage and passenger I would stiffen the rear suspension or get heavier springs.
As for tools, the following come to mind: tire repair kit with irons, an extra tube, as many size sockets and wrenches as possible or at least 10mm, screwdrivers or at least the #2 phillips, crescent wrench, vise grips, needle nose pliers, flashlight, testlight, electrical and duct tape, fuses, bulbs, a sparkplug, a plug wire, chain master link, oil, whatever chain lube you use.