Welcome to Eorzea Nyaria!
Firstly, you can actually get around that annoying 1000 character per post restriction by simply typing a few lines, posting that, then going back and editing the post and adding the rest of what you wanted to type into it (like I'm just doing now)
Really, it's personal preference - however, the main scenario is designed specifically to be able to level your first class to 50 pretty much exclusively so a lot of players indeed decide to hold off doing sidequests until they get their first class to 50 in order to then use them to level other classes. Having said that though, a lot of sidequests unlock special content (like the Challenge Log, dyeing armour etc) so they're worth unlocking straight away for that reason rather than holding off. It should also be noted there are other ways of levelling classes too so if you want to complete sidequests immediately don't feel bad about doing so!You also get a bonus to exp for all classes that are lower than your highest levelled one too so there is also that benefit to getting a class to 50 as quickly as possible.
Although dungeons are the fastest means of levelling, they are not the only means - try doing FATEs, your Hunting Log and levequests in addition to it if you're feeling burned out with running dungeons. Also at low levels, there is little reason to do dungeon roulette as the major bonus for them is only available if you do them as a level 50 character. If the Duty Roulette is consistently assigning you Sastasha, then it just means that a lot of new players are attempting it and needing to clear it (especially as you mentioned that you've had parties that keep wiping there - Sastasha is actually a really simple dungeon that most players now just run through). Sadly dungeons just get longer and more complicated, and there are a lot more you will have to do as part of the main scenario. But there is nothing forcing you to actually do them once you've already gone through it once.
Sadly when you first unlock a Job you don't actually get everything that really makes them worthwhile right at the start, but unlock gradually as you level and do the Job quests. A Job is a specialization in that class's role which makes them far more effective, while limiting what abilities you can equip from other classes (in WHM's case, healing). Additionally, it also boosts the controlling stat for that class (for WHM, that is MND). The initial ability yoou get at level 30 for it isn't usually that useful, but don't despair! Stick at it and eventually you'll realize that a Job is far superior to a class in every way. Most of the really useful abilities are gained later, like Regen, Holy and Benediction that you'll find are invaluable and will make things far more enjoyable. And a final benefit is between level 45 to 50 your Job quests will give you your artifact armour for that Job (AF), your first set of 'blue' gear that no only makes you look like that Job's appearance from older FF games (like, WHM AF is a white robe with red triangles), it's stats are extremely potent at that stage of the game and will help you out a great deal. So you Job is basically your class superpowered.
You can start to craft and gather if you so wish, there is no right or wrong to when you decide to get into it (I admit I haven't done much crafting and haven't done any gathering yet so someone else would be better placed to answer that question than me I'm sorry.).
Awww, you're fine - this is what this site is for after all! (And I enjoy helping out others just starting their journey in Eorzea so it's my pleasure to answer your questions.).
Again, it's entirely up to you how you level - some people like to try out all classes and Jobs and try to level them at the same time, while others like to level methodically, taking each to 50 one at a time. Having said that, it's worth levelling certain other classes at least partially in order to make use of abilities you can use with your main class/Job (in your case, WHM). WHM makes use of THM (Thaumaturge) and ACN (Arcanist) abilities, so levelling them to unlock some special abilities will be a great help. Specifically, taking THM to 26 for the ability Swiftcast if you haven't done so already is highly recommended, as the worth of this one ability alone cross classed on your WHM cannot be understated. It WILL help you as a healer!No question about it. What else you cross class is up to you, but as long as you have Swiftcast then all will be right with the world.
Anyway, hopefully this wall of text has helped you in your training in the ways of White Magic.![]()




You also get a bonus to exp for all classes that are lower than your highest levelled one too so there is also that benefit to getting a class to 50 as quickly as possible. 

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