I flew from Lima (sea level) to Cusco (3300m) and really struggled with acclimatisation. I don't know if it would have been different had I acclimatised along the way. Maybe? I struggled to walk up two flights of stairs without my heart hammering in my chest and felt like a short walk was a fast job. I had mild headaches and trouble sleeping. My husband, however, had no problem at all (he was a smoker back then, too. apparently smokers are used to dealing with less oxygen in their bloodstream? not sure if that's a myth or not). Anyway, you won't know your body deals with altitude until you get there.
Sounds like an amazing adventure ahead of you