Great Thread, as a ninja main myself i can completely see where you are coming from.
I have also only played two good cowboys so far while the rest got roundstart lightning strike parried and never really thought a move ahead. With Ninja you have to vary your combos and go for different routes depending on DI while cowboy has his "I combo now" teleport, which is nice but also doesnt encourage exploring your whole moveset and looking into what moves combo naturally into each other. While ninja also doesnt want to be in the air forever i feel like cowboy has an even harder time with air combos as his 3 slash specials are especially weak to DI and can easily end your combo.
The main thing i feel hinders cowboys though(which incidentally makes him the worst beginner character IMO) is that you need to be really good at the Yomi part of Yomi Hustle. Cowboy doesnt get really fast moves except his gun, pommel and lightning strike so he has trouble getting in(especially vs ninja). He needs to have read what i will do and make his choices in a way that doesnt let me whiff cancel out of them easily.
While teleport is a great combo tool both wizard and ninja can deny viable teleport space with their projectiles so it gets easier to read the teleport and punish it. Lightning strike is the only real tool cowboy has at range to get in as it is quick and it is a decent threat because of its fairly wide hitbox. Cowboy otherwise doesnt have a lot of tools to either keep pesky rushdown ninjas off of himself or get a hit in on those evasive wizards.
His 1000 Cuts can fill that role as it negates projectiles and makes his teleport a combo starter, but it costs 3 Bars and only one cowboy really saw how annoying that is. The other characters get some really good options from 1 level of super meter but cowboy only really has 1000 cuts because instant cancelling is just not necessary when you have teleport.
One great cowboy did his big lunge attack at a fair distance away so i thought it was safe to throw out a shuriken only for the cowboy to whiff cancel and be in perfect lightning strike range. While still using lightning strike i feel like this embodies what i mean about cowboy needing to be good at the Yomi part. Without hard reads or spending burst bar when they have more whiff cancels than me cowboy has a lot of trouble to get in on people. When they do they have their easy lightning strike times X -> teleport -> pommel -> lightning strike again combo which is not really all that fun to watch either. i love getting combod by wizards or other ninjas as the setup and flow feels really fun(and funny sometimes with all the wizard projectiles bouncing me around lol)
Cowboy needs *something* to threaten space better at longer ranges or he will always be on the defensive in a neutral environment. Cowboys best position atm is the default roundstart because its in lightning strike range, but afterwards they have to work real hard to get in.