Dodged a Bullet? . . . 1987 Nissan 15HP 2-stroke Outboard

. . . so, I'm only the second owner of this OB and up until last night have had no issues with it . . . usually crank it at home beforehand but didn't this time . . . get to the dock, and the recoil start won't budge, almost like it was in gear . . . checked the shifter, all is well . . . pulled the cover, turned the flywheel by hand (hard at first) . . . then cranked it up. Today I pulled the plugs (twin cylinder) and shot some oil into the cylinders and took a compression test, 140 lbs and holding on each cylinder.
Now, sometimes I don't disconnect the fuel line and let the float bowl run out of fuel before trailering but the last time I did . . . so I'm wondering if this is a good idea, since low/no fuel means no oil in cylinders during storage . . . or do I have bigger fish to fry? (no pun)

. . . the main reason I ever ran the float bowl dry is because sometimes the float needle would "stick" in the seat during months of storage.

I feel like no oil in the cylinders is probably better than ethanol gunking up in your carb.

Not sure how you winterize your OB, but careful attention at the end of the season (including fogging and and properly treated fuel) makes coming out of hibernation much less problematic.

I don't think you have anything to worry about. It surely wasn't carb related. Sounds like something was bound up.
I don't run my carbs dry and have never had a problem. Some guys believe in running them dry so do whatever you think is best.