Im honestly not bothered by Pit when it comes to this match up I mean you play agaisnt a Falco that feels worse to me cause he can stay on the run with his lasers, Pit can't do that with his Arrows. I was playing a very good Game & Watch a few days ago I mean he could do the 9 on demand he keeped trying to get me with it. Anyway to me this match was more about mind games and learning to correctly shield grab his B-air. Fortress was still king in this match up and the bucket wasn't an issue at all with useing fire breath really I alway hit him with a fire breath as he tryed to come down on me then he'd try to go into Bucket I'd quicly stop before he'd get drop and run up and side-b him. To me the match up felt even since we keept going back and forth on who won and I lost track of who actually won the most round in the end. Its true that most people don't know how to approach Bowser they just assume im going to be slow and an easy target.
A good Ike player gives me a lot of trouble. When I say a goiod Ike player I mean a player that can follow up Ike mad good one two three punch into mid grabs and other combos. I've found that through playing Ike his Jabs will completely out pace my jabs even if I get the first hit. Plus I have no way to edge guard him when he's coming up with an up-B doing so just gets me hurt or risks getting draged down. Plus out of all of the other characters his f-air seems to be just be slighty better than mine which is a huge problem on approaching for me. My biggest tools on killing him would be Fortress, Fire breath, up-tlit, Side-B, Grabs, N-air, and rarely D- smash. Trying to come from unerneath Ike for a Up-air is more risky than trying that with lucario . If have suggestions for dealing with Ike I'd like to know.
im talking with personal experience. against ike, you should always remain on the ground except on sneaky SH side-B. what most ikes(good ikes) do is jab cancel, and do retrieving F-airs. if see the ike jump, get ready to power shield it and punish. His F-air is easy to see coming but sometimes tricky punishing it. if he stays on the ground hoping to jab you to death (or atleast 20%) fire. you said he makes it hard for you to approach, but you really don't need to. Let him come to you. if your fire does even 1%, your in the lead. dont go all bruce lee and fight his F-air with yours.
some other tips that i find useful.
-when ike is recovering space your fire so that it hits off the edge but ike's aether has no chance of hitting you. if it hits, ike starts falling and the person on reaction do aether too fast, leaving room for more fire or other punishment.
-if the ike gets predictable with his F-airs, its not a bad idea to run right under his jump and up-smash. be careful because his F-air still hits from behind.
-if youre near the edge, try not to roll behind him, or youll most likely eat an up-smash.
-stay in your shield and up-B, but thats general bowser info.
-if you're at 100% or higher and you see ike staring the opposite way (not facing you) he is going to do a SH B-air. It comes out fast and can kill.
-DONT GET HIT BY HIS SIDE SMASH.
Hope that helps.