In my opinion WY could make a low at any time for a nice rally. In Elliott terms it should eventually rally well above 74. I had previously referred to WY for the purpose of selling Feb puts. I think selling the Feb 55 puts is not a bad idea. Even if the stock gets put to the seller, the seller has a high probability of being able to sell the stock higher than 55, and fairly soon after expiration, in my opinion.
You are talking about something different. This market in general has me scared to death. When this market tops, the downside potential to this individual is both breathtaking and quite frightening. In Elliott terms it can be counted very clearly that the Dow has completed 5 waves up from the 1998 low on the monthly chart. It is also possible the entire bull market is about to end. I say that not to frighten you, but in order to ask yourself a question. If I have WY and it drops 50% or more, how much is that going to bother me?
Having said that, the weekly chart suggests WY is at or near a low. The monthly chart, in my opinion, is more bearish, meaning the overall decline in WY could last several more months. Obviously, I could be wrong. The risk is high enough on the monthly chart where I would not buy and hold here. But, that is my opinion. The stochastics, on the weekly or the monthly, does not suggest a huge rally is coming from here. Although the weekly is close. WY can have a big move from here, but the current stochastics lower the probability of that happening from right here in my view.
Below this area, I have the next major levels of support at about 46, 42 and then 37(monthly chart). I'm not implying the stock is going to these levels, particularly 37, but that is a level of support.
Your idea of not buying all at once may not be a bad idea, should you decide to buy. Hope this has been helpful to you.