Well, you only have to time it 1.5 times because you can always sell before expiration, although there is that upper bound. If it doesn't look like it panning out, and you called wrong, you can get out and recoup some money.

You'd have to approach it more like swing trading than buy-and-hold type strategy, unless you're aiming for something like next year.

Presumably you are in fact bearish going into the trade. If not, you probably shouldn't have traded the strategy in the first place.