I am a support main, so I don't know most of these things myself, but I'll offer the advice I've heard from others.
Helping your jungler depends on what you mean.
If you are blue side, and your jungler wants to start blue buff, you should help leash him on blue so that he is healthier for the rest of his clear so he can gank. I assume you know this, but just checking.
If you are top lane, your jungler is clearing is top side, and you notice the enemy jungler attacking him, then yes, you should help him.
If you are top lane and your jungler is invading the enemy jungle, then you should be paying attention to your map to see if he needs help, but otherwise you should be pushing your lane (killing enemy minions quickly) so that your laner can't leave lane without losing a lot of minion gold. If the enemy laner does leave lane to kill your jungler, you need to follow and help your jungler.
Other than that, you really don't need to help your jungler much. You can, but you may miss minions in lane, which means lost gold and lost experience. There are times when losing some minions is fine, but most times you want to minimize how many minions you miss.
When to Roam
As a top laner, normally you take TP so you can roam and help your team. I use the term roam to refer to going to another lane during laning phase, because people expect you to be in your lane during this phase, so that's when a roam can catch people off guard. You have a few choices of when to roam.
- You can roam when you push the minion wave to the enemy tower, reason being is because most top laners are melee (there are exceptions), and can't really poke the enemy while they CS under tower. And since the wave is wiping at the enemy tower, it will eventually bounce back to the middle of the lane so you roaming at this moment doesn't hurt your CS because the enemy tower will ensure that the enemy minions kill your ally minions faster.
If you roam at this point, I recommend just staying around top side jungle, try to get some deep wards in the enemy jungle if you can do it safely, or walk to mid lane. Only TP bot during these moments if you really think this will work out, because you'll probably lose a lot. Minimum you'll probably lose a wave or 2 of CS. Depending on the enemy top laner though, you could lose your tower.
There are exceptions to this, like Illaoi and Kayle and others, since they have range abilities that they can use to harass the enemy under there tower without taking tower aggro. So you have to decide whether to stay and harass your laner or roam.
- You can roam when you back the first few times. The reason this works well is because your laner expects you to be away for a while, so they might not warn their team that you aren't in lane, which gives your opportunity to possibly surprise the enemy, and then just TP top. Pantheon does this a lot once he hits 6, backing, ulting bot or mid, and then heading back top afterwards.
If you roam now, you can choose which lane to go to, but this might be a good time to roam bot lane, since it is a very important lane to snowball. This is also a good time to possibly get dragon, so getting bot lane to help will make this easier.
Now, one thing to remember is that Kayle and Illaoi aren't great gankers. Kayle has an on demand slow, which is ok, but not great ganking potential. Illaoi has a delayed slow, and does little damage without tentacles already spawned in a lane, so she doesn't offer much gank ability unless the enemy is literally under your teams tower. The only time I would really leave my lane is if your team is in trouble, because more often than not, these two character are better in lane. Illaoi has powerful area control with tentacles spawned, and Kayle just wants more gold to become as strong as possible which is easily accomplished by just farming.
Jungling
Jungling is it's own part of the game and it varies greatly from game to game. Some games you can just farm your jungle all game because your team doesn't need the help, and other times your team could use your help, and other times the enemy team is invading you constantly making your job impossible.
It's a role that you should be planning out though for multiple situations. You should look at your laners and determine who you want to help. For instance, a Yasuo will be pushing his lane hard, so if he is on the enemy team, you know he'll probably be pushed up which is a good gank opportunity. You should be keeping things like this in mind and always be looking at your mini map to determine which laners might need your help.
The easiest thing to do is start on your bot side buff, clear wolves, and then your other buff. That should get you level 3, and leave you on the top side of your jungle with both buffs still working. This is a good time to look for a gank because autoing with red buff slows people, which may be all you need to blow someone's flash.
Now, this is just general advice. Shyvana, for instance, is a farming jungler with no CC outside of her ult. Since she clears very fast, most people just farm on her instead of ganking much. Obviously you can gank depending on where the enemy is in the lane, but this generally isn't what she focuses on because it isn't her strength. Fiddle has his fear, but that's about it. He still needs to run into lane to get the fear off, and even then, he doesn't have much damage to help kill the laner early on. Ganking with Fiddle pre-6 is kinda difficult, but not impossible.
The other thing to worry about is what happens if the enemy jungler appears and counter ganks the lane you are ganking. Can you and your laner fight off the two enemies?
And this is all what I know from not playing these roles. There are probably plenty of other things that I'm completely ignorant about these roles.