Yeah, dollar cost averaging may be the way to go. There have been a number of times where I've thought to myself "just buy some already" but so far I'm holding out a bit longer to see what happens.
Good luck with the learning! With all the issues ETH contracts have had lately, I'm weary to go there. I'd hate to someday be responsible for someone losing money due to a software bug in one of my contracts. C++ may be a bit much to learn, but I'm starting to look forward to the challenge as EOS becomes more real to me.
RE: Could EOS Become the Most Widely Distributed ICO Ever?