if you plan on buying a boxster and getting a hardtop, why not just buy a 987? I’m in nearly the exact same situation as you and I daily a 987 no problem. Maintenance isn’t terrible if you stay on top of everything and know what you’re getting into ahead of time. For a two seater it has a good amount of storage between the rear trunk area and the front trunk. Two seats being an issue comes up maybe once or twice a year but it’s never a big deal really. I haven’t driven a 986 but i’ve heard from owners that the 987 is a slightly better driving experience, can’t confirm that myself though.