I've got both a XD SubCompact and a Glock 19. I carry the XD appendix carry, the Glock about 4:00, both IWB. The XD is easier to reholster since I can keep pressure off of the grip safety by gripping the pistol with my fingers under the trigger guard and thumb on the back of the slide.
Reholstering the Glock is a very slow process for me since I'm paranoid about shooting myself in the stern. I have to verify the location of everything (fingers, shirt, holster parts, etc) before pushing down on the gun.
Love shooting both, but I'm much more conscious of the possibility of accident with the Glock. Both pistols are less comfortable for me than my "safety lever" pistols. I can never envision using either as a "pillow gun", something I've done with various other safety equipped autos for many years.
My xd45 sleeps between my matress and box spring and when I put it up at night, I use a similar method. Just grip it a little funny and slide it in. As far as reholstering, I've never worried. Situational awareness is key. I'm actually more paranoid when I mess with my M&P9c with safety, because it's easy to knock off, and I would rather know it isn't there that wonder if it's on or not. The M&P wont have a safety much longer. Millions of glocks ride in LEO holsters everyday and they seem to do fine.