Of course it will drop again.
I would consider $1250 as a near certainty at some point in the next six months, even if this rally reaches all the way to $3000.
And as the poster above me mentioned, sell a portion. Sell even just 20% of what you plan on selling at $2000, then list another 50% of what you planned at $1998, then list some more at $2100, 2200, etc.
Never go all in, or all out.
It can't hurt. I went all in at 300 and 600 and I've made some nice profits, still holding. Depends mostly if you like taking risks or going safe, personally I like taking risks with crypto as I've made far more doing risky shit than planning out something and following the plan. Just sell when you feel comfortable with your profits and buy something nice to feel better; historically, if you've bought coins before this month at any exchange price and sold right now, you'd have made money. This is including Gox prices which were incredibly inflated.