As far as I'm aware, the number of overall drops accumulated is insignificant and one can drop instantly back to back or at any other point premature to the drop timer expiring. Such control sacrifices the temporary stat boosts available as drop bonuses but is necessary when completing the special portals for the End of Pain Keyblade.
For trouble with running out of drop time during battles, equip drop-me-nots to extend it.
I'm in Proud Mode as well and here is how I've made it kind of a joke--so far.
- I achieved my first clear in Standard Mode and entered Proud Mode with New Game +.
New Game + allows one to carry over their spirits from a clear file to a new one. This can make moves normally unavailable until later in the game available in the beginning.
I had Superglide, Dark Splicer, Dark Break, Faith and Sonic Blade before even leaving Traverse Town the first time.
- While working on the first three special portals and acquiring the above moves, I grinded in the fifth district of Traverse Town until level 30.
- Out of favoritism, I visit the first cluster of worlds in reverse order. I start with the most difficult, Prankster's Paradise. Consequentially, the Dream Eater's were a bit of a bitch at first, particularly on Riku's end. So I grinded again until level 40. I finished both boss battles in 30 seconds to a minute. After finishing all special portals I left at level 43.
Next was The Grid. I had Rinzler defeated seconds after the battle turned upside down for the first time. Riku's boss battle took a bit longer but was just as easy.
I am now in La Cite Des Cloches at level 47 and the Nightmare that chases Riku across the bridge and through the outskirts hit me several times but barely did damage.
The most difficult two bosses for me whom I haven't faced yet in Proud Mode and I'm not looking forward to it are the damn Spellican in Sora's SoS and Mystery Cloaked Nightmare dude, the first of the string of final bosses in Riku's TWTNW.
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