Don't disagree that checking deck is a good idea but it is unusual for 95" pistons to sit above the deck; it happens but not very often in my experience. If you cannot detect whether the piston is above/below the deck without measuring, by all means check. I will bet a six pack yours will sit below the deck.

Squish from .030" to .040" is OK, I just like getting as close to .030" as I can.
If pistons were sitting above the deck as in B'dude's example of .002" and .003", I probably would have used a .036" head gasket where he went with a .040" unless there was another issue that dictated a more conservative approach. No right or wrong, just one is a more conservative approach than the other.

 

We were already pushing the compression in that particular motor. In that case, a 037 squish kept the cr within projections, and the owner of the bike was happy with the results. Had the 040 gaskets on hand, would have had to order the 036s, so he asked me to put it together with the 040s. I'm not claiming that being above deck is common, nor am I claiming that being 008 or deeper down is common, just providing a couple of examples.

 

Who sells the .027 MLS Cometics? All I keep seeing from suppliers are the .030 and .040 MLS's

 

Buy direct from Cometic. They used to sell an MLS .027" gasket but I don't see it on their website any longer but did see a .027" copper head gasket. Call Cometic; pretty sure they will have what you need. I would not get too hung up on squish, anything from .030" to .040" will be fine.