Any way I can help a new player have a decent experience in this game?
I was trying to bring someone over (a League player), but the experience was awful. He was forced into a 15 minute tutorial focusing on things he already knew, so he had to get through that before we could actually play together. When he did, I got him into a bot game, and he was immediately overburdened by the amount of heroes. After a few minutes of flipping through, we decided on Clockwork for him and Crystal Maiden for me - I was planning on giving him the mana to spam out clockworks spells and let him have fun ganking.
Then somehow DotA auto-binded his Teamspeak push-to-talk to its own push-to-talk, so we had to spend a few minutes fixing that. At this point I knew he'd be hopelessly under-leveled in lane, so we restarted the match. Then came the items - "There's like a thousand items. Why do some need a secret shop? You cant be serious, that was a horrible design decision! What do I get? Where is the core items list?" etc. I'm not really a big dota player myself, so I pointed him towards tangos/stoutshield/boots/bracers, the usual kind of stuff.
So we get it lane. Almost immediately he's tanking creep hits (League minions are much weaker), so I warn him about that. The lane gets pushed, and we're at the tower. He tries to hit the tower, DotA's tower rules are different so he loses half his HP before getting away. Then the Venge/Bountyhunter kill him.
Anyways, to not make this a page-long reply, he had a real tough time with all the options available in DotA - it's too complicated. The map is too big, there are too many items, there are too many heroes, what the hell is this flying donkey doing here, etc. He rants in Skype about how horrible of a time he had, and I'm left unsure of what I could do to help the problem.