The game is about how many you own and can keep in your possession. If you own 1000 BTC, you are well positioned, but it is expensive to gain that position if you start now. If you owned 1000 BTC five years ago, it is equally good as 1000 BTC now, only if you have managed to keep it from theft, hack, taxman, your own mistakes in storage, and most importantly from your urge to sell.
Many reading this have 1000 XMR, or even much more. In five years, or less, it might have equal value as 1000 BTC now. Statistically, an extremely small fraction of people manage to do it, though.
I believe it's prudent to budget in advance that half of the remaining coins are lost, every time the price rises x10. So the ones who wish to have the coveted 1000 XMR when the price hits $5k, should buy 10k now.
Hmm... it seems that XMR is more mature now than BTC when I heard of it. It has 50 times higher market cap as well...
I like this strategy. Lot of people might say "SELL NOW", price may go down, which is certainly a probable outcome. As for me, I decided I want to have X amount of Monero and I try to adhere around that number. There was a brief time I played the sell because I thought it would go lower, then ended up buying back higher, then the price went lower...personally I don't want that stress and it causes me to make bad decisions. This is the opposite advice some people would give you (don't get attached to any asset, etc). I think you can get attached as long as you ensure the decision is right for you.
Personally, I like a variation of buy and hold that rpietila discussed for Bitcoin awhile back:
This way you get to take some profits, you hold a meaningful amount long term and if you want to buy back in on the dips, you have the funds to do so. Although no investment is 100% stressfree, this method has worked for my holdings.