Nah you don't fall into the man baby category. I know guys in their 30's who have their parents paying for everything. I know a guy who is 36 who admitted he has never bought toilet paper in his life and that was a guy with a Masters degree in Computer Engineering.
You have thought this all out very well and I feel like you have a very good grasp of what could likely happen and then what we could see with the next surge.
The Bitcoin halving in 2020 could be the next major catalyst to cause a mind blowing run. I hope we don't have to wait that long but we might have to.
Even with STEEM we experienced a 98% loss of value from the highs in mid 2016 to the lows in early 2017 and then it surged again. Sometimes stuff has to go so low in people's perception that they throw Vegas gambling type money at it that they are truly willing to just take a shot in the dark in a way.
The fact is we will 100% have another crypto surge and with each boom and bust it confirms its strength and longevity and becomes "less risky." I feel that there are certain cryptos that have sort of became reserve assets that have secured their place in history.
Bitcoin, Litecoin, Ethereum, Monero ...... but then also EOS, Bitcoin Cash, Dash and a few other have likely secured their future as well.
I noticed you haven't listed Steem as secured. In addition to most of those above (except Monero and Dash), I have a little Bitshares too in case governments start shutting down exchanges out of panic.
STEEM is likely safe for the long run and technology wise this really is a top 5 - 10 crypto but you have to have a wide and fair distribution for a crypto to succeed and STEEM didn't have that. It has weighed heavy on it and continues to be an ongoing issue.
EOS had a more fair distribution but there are still governance questions and how that will all work out in the end.
I have some BitShares as well but I worry that a decentralized exchange will be built on EOS very soon and will render BitShares "OLD"
We should be ok with STEEM as long as our timing is decent. Easier said than done but realize that the initial founders and early ninja miners got such an extreme amount of STEEM that they can always dump hard on us and also people start to depend on STEEM to earn so as payouts go down and they start depending on it then they can be forced to dump even more if they started to depend on it for bills. It can make the down periods that much more steep.