Your reads are telling you to squeeze, so go for it. Shoving is fine, and so is raising to $100 total.
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should I always be attacking when these squeeze plays present themselves?
Always?... It depends upon your reads. Some players will not let you get away with this, others will always let you get away with it. Again, just consider your image and your reads and go with whatever you deduce to be the best action.
Just my opinion...