There are levels of risk with any connection. The longer the time between flights, the less the risk. Earlier in the day, the less the risk. Originating early AM flight is a plane that came in the night before, less risk of a departure delay. If originating aircraft is an inbound redeye flight, risk increases. Two day advance weather looks bad at either point of origin or connection point, risk very high. And the consequences of a missed connection range from low to high depending on if it is crunch time holiday travel, school vacation week etc.
I will take short time connections if the risk can be mitigated...many subsequent flights to my destination with likely availability.