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 Yeah go for. I know someone who freezes apples on purpose and presses them and ferments them into cider and the result it excellent, its the same idea as ice wine. He is freezing them and not pressing them months later but I can' really see it being any different at all. 
 
The only downside is the energy and time cost. The plus sides are that usually you don't have to scrat (mill the fruit to small pieces) and any undeveloped sugars like starches are broken down with the freeze /thaw. This really makes for a much higher quality juice which ferments better and just has a much cleaner flavour after fermentation, hence why its done at all.

 
 Does your buddy freeze them whole? Does he just drop them in the freezer with no container or anything else? Thanks for the info! 
 Yeah whole, he usually just puts them in a crate for ease of removal. He has another freezer that's clearly for small ice-creams and it doesn't allow for access of a crate. However he was doing eating apples when I saw his setup, if you are doing pears they will likely collapse under their own weight when defrosting so load then straight into the press and/ or anothercontainer to defrost there to catch the juice. 

Also you could potentially macerate them before (or after) freezing if you wanted to try it he isn't doing that. Perhaps it's too messy to use a mill and just smashing it up a bit by hand will work.
     Normally if you leave the macerated pomace to stand for 12-24 hours at room temperature there is an enzymatic process that helps it separate. You can then pour the pomace into the press and a lot of juice just comes straight through the press bag, which if you have a small press can make it quicker despite the time delay. So if you are pressing over a couple of days it might be worth trying, the effect is more pronounced with pears over apples  
 I'll be grinding them up in a grinder over the press and into a cloth bag. This is good news! I was worried the pears would not freeze fast enough when I put them all in the freezer. I'm dedicating the freezer to the pears.