You raise a lot of topics, @BarryWuzHere. Let me try to unpack some of the themes.
5* and 4*
As a general rule a 4* at 4/70 is more effective than a 5* at 3/70, but uses the same rare mats and far less food and feeders. There are exceptions to that generalization, though. Heroes whose primary benefit is the special effects – like healing – are solid at 3/70. Exceptionally good heroes like Alasie are also worthwhile at 3/70. Obakan and Kadilen fit into neither category, so I’d defer on them.
Looking at your 4* color items, you can apply a rule-of-thumb that you’ll get three 3* mats for each 4* mat. For example, you’ll likely get three trap tools for each tabard, three hidden blades for each ring, etc. How to use this info? You need 4 more rings for Gravemaker, and you’ll likely get 4*3=12 more hidden blades by then. You’ll need 8 of those for Gravemaker, so you can spend whatever blades you have plus four more without much risk that you’ll be short of blades for GM.
Same-color training
I’ve written this many times before, but when you are building out your team and have many projects in front of you, train exclusively matched-color. Not only does this double the odds of raising the special skill, but it gives a 20% premium on experience. Any one hero will ascend more slowly following this discipline, but your whole team will rise faster. Always have a project in each color.
Yellow choices
Wu Kong makes a dramatic difference on your titan scores, and getting high-tier (IX or above) titan loot is how you get the stream of rare mats flowing. Wu should get your next set of orbs and first gloves.
Red choices
Finish up Scarlett, then work on Boldtusk. Boldtusk is very useful in all sorts of situations. I’d give him the first set of hidden blades and the second gloves. Lancelot is a glass cannon–hits hard, dies fast–and his attack buff collides with Boldtusk’s. Gormek is the opposite, but his armor debuff skill is so valuable, I’d bring him up before Lancelot to use against purple and green titans.
Gravemaker is a top-shelf hero that you will want on your team. Keep an eye on your ring count, and when you’ve got four, shift over to raising him up to 3/70 to be ready to push him on once you get ring #6. The other thing to work on for Gravemaker is getting and leveling a 4* red mana troop. At level 11, that troop will power up GM with only six red tiles (or just three ghosted), which happens WAY more often than 7 (okay, 6.5) tiles.
Blue choices
Alasie is a really solid hero and should get your first set of scopes. Trouble is, you’re a long way from getting those. Nonetheless, I would raise her to 3/70 as your blue project (giving her your third glove), followed by Sonya. It would be really great if you could land a Grimm.
Purple choices
I am not a fan of Obakan; I think he’s the weakest of the standard-issue 5* heroes. I’d bring up Cyprian while you wait for gloves #4 for Sabina. I’d hold those tabards until you get a 5* that is worthy of them, ideally Sartana or Panther, but even Quintus or Domitia.
Green choices
Unless you love playing the challenge events, I’d put Jack O’Hare on hold in favor of Melendor. More healers is always better for Alliance Wars. Kadilen is not a bad 5*; when you get a couple more tonics, reassess. I would ascend next month’s HotM, Gregorion, before Kadilen.