Akira Toriyama articles - the articles, comments and such that mention things about super, the super saiyan states, and what not, are mostly gathered from the various published interviews of toriyama. Some of them can be found in the DB wikia if you look.
---------------------
Super saiyan - Not necesarrily, remember they were able to find a way to improve the basic super saiyan transformation by three methods if ou think about it and considering what toriyama said about the super saiyan 2 and 3 being stronger variations of the basic form.
We have increased energy output variations; Ascended and Ultra forms. We have a controlled, natural variation; Full powered form. And then we have increased energy variations; SSJ 2 &3.
So if you were to scale it back to SSJ1 and think about it, you could technically apply what you learned of the other variations to make the base form that much stronger. It probably helps that they obtained the forms to begin with, that way their bodies know the increases in power so it can be applied to the base form. rmemeber a lot of these numbers were just thrown out there, they don't really mean a damn thing in DBZ, so keeping that in mind, it makes sense.
Here
http://dragonball.wikia.com/wiki/Super_Saiyan
look at the end of the paragraph under the power and useage area, between the pictures of long haired ssj gohan in the HBTC and ssj future gohan, to see it. It states toriyama's word on the super saiyan form and gives a cited source for it, tag 35.
--------------------------------------
Gohan - He probably didn't transform because he thought he probably couldn't. Remember old kai told him to power up like he was going super saiyan in order to finally bring out his hidden power to the surface. So he might have thought he lost it somehow, like the power had been absorbed into his new form. That by itself would makes sense, seeing as how ultimate gohan was the strongest character up to that point, even more than gotenks absorbed super buu, who used picollo's knowledge of gohan and tactics to outsmart gohan rather than face him head on in a struggle of might.
He likely did a little bit of training after buu was finished to acclimate back to normal life with his new power, so he wouldn't break everything, and discovered he still had super saiyan.
----------------------------------
LSSJ - but then that would defeat the purpose of there being a LSSJ... that there's only one, in like, every 1000 years. I'll be honest, I'm resistant to even having broly in the rp until it was time to have brought him in, and I'm especially resistant to there being another LSSJ roaming around.
----------------------------------
Freiza - Nope, freiza was a spoiled brat because of his power, he had a s**t ton of power that just came to him, backed up by a wealth of talent, all of which was squandered because he never trained.
Remember cooler's personality type is one that won't allow him to trail behind others willy nilly, he likely put in decades of hard training just to get to the point where he was in cooler's revenge. Yes we see a true form cooler trouncing on goku, but remember, goku wasn't in his SSJ form for that, and even in his combat form, cooler wasn't even really a challenge for goku once he went SSJ.
So while yeah, at the time, freiza was stronger than cooler, while they were both in their true forms, but cooler probably was stronger than namek time line freiza while he was in his combat form. But as we saw in resurrecton of F, if freiza put any kind of training into his power, his true form's power would be absolutely monstrous, enough so he wouldn't even need a combat form like cooler.