1. You can get bless for every character by interacting with the statue. (Not sure if it's new from this patch or if it was there before.) Only the main "characters" go in the weird place but companions still can get Bless by having them interact with the statue.
2. I was stealing the lower cost books at 3 thievery and the higher cost books at 4 thievery (I bought gloves that increase my Thievery by 1. ;D). Thievery also allows to steal more than just books too. If you can't steal a book, steal something else so you can afford those books.
You can steal good starter armors and weapons easily in Fort Joy. There is a very good starter leather chest on Griff table you can steal if you are smart enough to distract the NPCs with your companions while your thief sneak past the detection cones. Me and my friend always had "just the right amount of money" readily available to get the skill books we needed to get through each part.
3. Classic difficulty IS supposed to be hard and challenging. Like I mentioned in my OP, I do not know about Explorer mode and that's not what I give my feedback on. If Explorer mode is too hard, too costly, etc. then Explorer mode needs a difficulty balancing.
4. If the enemy seems to always start before you, then Invest in Wits.

Strength, Finesse and Intelligence may be the most useful stats but they aren't the be all, end all. My wizard almost always starts first at 15 Wits and one cast of Burn my Eyes will make any of your character first on the turn. You can actually have a character play twice in a row using Burn my Eyes on whoever is last to play on your team for the round and the next round they'll be first, effectively playing twice in a row. A two handed warrior can easily wipe an entire team of enemies using that tactic. Use your 3 other characters to weaken the Physical Armor of enemies, teleport them close to your warrior and apply Encourage + Burn my eyes to the Warrior. He'll have 2 turns to wipe the enemy team and using Warlord talent, Adrenaline, Haste, etc. You can get upward to 20 action points worth of attacks in. One well-placed Rage and the fight will be over before you can say WTF.
5. Buff before engaging when you know you are about to fight.
6. Disengage if you get ambushed... There is nothing wrong with disengaging back to the nearest teleportation statue. If you don't want to meta-game, this is the option you are given to do that!
7. Invest in Leadership... It's freaking good.
8. Invest 1 point in other combat abilities for level 1 skills that synergize well with your character build. Adrenaline, Rage, Teleportation, Burn my Eyes, First Aid, Armor of Frost and Fortify are all good example of abilities that almost any character can benefit from. You haven't truly seen glory until you see a Wizard with Rage and Savage Sortilege using a Source ability.
9. Use the "delay turn" option to reorder whom amongst your character will play first and get the most out of your support abilities or to simply let the enemy do the leg work and close the gap for you.
10. The most important point: Use items! Potions, scrolls, grenades and special arrows. One Lightning Discharge scroll will quite literally change the battle from a complete disaster to an heroic win.
Once again, if Explorer mode is too hard, then yes, by all means, tone it down. But to me, Classic mode is fine and I want Tactician mode to be even harder because the current Classic mode, while challenging, isn't enough for me. That's what difficulty modes are there for.
P.S. No offense to my friend, but I find coop to be harder beside being able to customize more than 1 character at the start for the fact that each player wants to play their way and synergy isn't as easily achieved in a party as it would in single player. And sometimes, both you and your friend have different plan in mind which ends up screwing the both of you.