Dude yes just ask him out. You guys have totally developed a relationship that isn't. I don't get how you can text about surgeries and family member's deaths but no one asks the other person out.
The day after my father died, I hung out at a guy's house. Granted, I flew back home within 24 hours of my dad passing because I'm not local. There was nothing to do since we had already cleared out my dad's apartment months ago and I was on bereavement leave for the next week and funeral was in a different state a few days later. So we chilled, watched football, and drank. It was a good break.