It depends on the screening location. You can clear TSA with three laptops, two ten ounce bottles of water, and a bottle opener without question in the precheck lane accidentally. (Whoops). Or you can have them pull out a single surface pro 3 because it "looks like a laptop on the X-ray".

I'm a gadgethead, but I generally tell the TSO that I have "more than one laptop" and then divest any laptops over one to a separate screening bin per laptop. This almost always avoids secondary.

Some TSOs don't care about multiple laptops in the same bag while others will then pick apart the entire bag because "the x-ray was unclear". When they insist that I don't have to divest despite multiple laptops, it's about 50/50. Most TSOs are willing to give you a bin if you ask.