Lock in some wins and maybe miss the boat; or pick up an oar and risk going down with the ship?

There's a sweet, third option.

You could do both at the same time.
You could buy an asset that will appreciate in value if/when STEEM moons; which also has a firm floor.

My Steem account has a lot of value hiding in a lot of different places.

There are the balances, obviously.
Then there are the followers. A few big names there.
There's the reputation score; for what its worth.
There are the Steem-engine tokens.
Then there's this number: # 47,680

There were fewer than 50,000 people on chain when I saw enough potential here to start up an account, and even though creating the account was free, that number is now valuable. Even if I powered down, posted crap until my reputation was zero and sold everything, an account that early would still sell quite well.
How did something that cost me so little become more valuable over time?

I also have a decent stack of silver coins. Having @bearone's lovely design stamped on them didn't cost much at the time, but now it makes them far more valuable than generic 1 oz coins, and they'll never be worth less.

What a magnificent each way bet. If STEEM takes off in the next few years, I can turn a handsome profit selling social proof of being part of the ecosystem back in 2017; and if it doesn't, I still have a lovely, rare, 1oz .999 silver coin.

I jumped in again in 2018; and just placed my order for 2019 coins.

Not only are they a magnificent each-way bet, but the coins are numbered, and providing proof you hold the previous year's number gives first option on that number each year.

_{Proof I should dust more often.}

So not only could I sell #8 for 2017, 2018 and 2019, I'd also be selling the rights to order #8 every year indefinitely.

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What did I pay for this incredible windfall?

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Roughly the same price as if I'd bought three 1 oz koalas from Perth mint, which would be worth 3 oz of silver today.
How is that not an incredible deal?

We're halfway through the presale period, and the organiser, @raybrockman has just posted that around 30 of the first 100 numbers are likely to be available; as the 2018 owners haven't laid claim by ordering them again this year.

If you're sure we're going to moon, then power up.
If you're sure we're dead in the water, power down and sell.

If you don't know what the future holds, there's a sweet third option.