Yes, with only 21 million of them there is no level of success small enough to give a stable price under $1000. So the only possibility for BTC not to reach $1000 is if it goes to 0. Which isn't impossible of course.
You're thinking really long term.
The block reward will get cut in half in 4 years and by that time it'll be worth around $1000 for sure.
There'll be bitcoin atms, bitcoin smart cards, there'll be more places that accept bitcoins like Germany.
I think the proper question is if it will reach $1000 before that.
Yes, but that is the way to deal with novel investments like Bitcoins in my opinion. Don't worry about ups and downs, don't try to time the market, and for the love of god, don't trust technical analysis.
I don't think that block reward halvings will affect the price too much, as for the time frame, I'd be surprised if the price isn't at $2k within two years. We'll soon get to the situation again when the sellers start to disappear. Not very healthy but most sellers seem to have a much higher price in mind.