I think we may not see a sudden massive short squeeze but rather a prolonged and small short squeeze taking place over days or even weeks. That is the best thing for the market right now, because high short interest is the best plunge protection. BTC price simply won't drop significantly as long as short interest remains very high.
In a market that is slowly going up, eventually all shorts need to cover. If this scenario plays out then moving average lines will slowly turn up, golden MA crossovers will take place, ichimoku cloud will improve, etc. So, high short interest will keep on improving the overall condition of the market.
The best strategy if you are a BTC bull, in my opinion, is to keep a core position long in the market, and only trade with a small percentage of your account (if at all). This is because right now it seems that the risk is to the upside, not to the downside - meaning that if you do not remain long, you may miss out on sudden gains in the market. Such a strategy will also allow you to sit back and relax.
This market right now simply favours the bulls.
I'm even starting thinking that we may have seen the bottom in this market - or rather the bottom line (around USD 6,000 - or 5,850 to be more precise).
Best of luck with your trading/investing.