Regular Play

Four months have passed since we began playing 5e D&D on Roll20. It has been an interesting process. Those first awkward moments trying to learn how to find anything through the interface, let alone roll a dice have morphed into pretty sophisticated use of all the system has to offer. It has been a process, but it has been fun.
There are several facets of the experience that are noteworthy. For years, we have spoken of the need to play more often. With Roll20 we have been able to play four or five sessions of one campaign, and three more in a second. Eight sessions in 16 weeks you say... not a great percentage... On the face, the numbers are deceptive. There are vacations, concerts, moving, and general coordination of schedules involved that have influenced the whole. We have forced this situation upon ourselves, and fought to make it more regular. While it took time to get into a rhythm, it has paid off in allowing us to play more in these few months than we can usually find in the course of a year. It is a great way to get together when distance keeps you separate.
Another advantage of playing regularly shows in the flow of play once engaged. Some weeks we've been able to play consecutively, others have been after a week or two of inactivity. Those can take 30 minutes or more to get everyone together, get settled, and remember where we left off. When you only allot two hours a week for play, that is a significant loss. Playing regularly helps keep everyone engaged in the game, and able to spring back into the gameplay quickly.
It is also helpful in terms of role playing. Each encounter allows the nuances of the character to emerge, and regular play lets you find that playable element and develop it consistently. This is an interesting and critical part of the game. We've often fallen into pretty narrow types with our characters because of the infrequent game sessions we have, and it has been jarring at times to break out of that routine. At times we've been able to play in consecutive weeks, and the out of combat moments have blossomed into some more memorable actions and sessions as a result. It has allowed for better interaction within the party as well.
There is a weird dynamic within any D&D game, and one of the aspects of this is that each session can take on the personality of one of the players. Even when you try to account for this by designing elements to focus on one character, it is often another that steps out to dominate that moment. It is a fascinating part of the interplay within the game. I've found that the more fractured the scheduling, the more disparate these moments become. With longer breaks, it is more difficult for everyone to fall into character. When there is better continuity of play, the party dynamic rises on the individual styles and provides a more balanced, harmonic session.
I'm looking forward to learning more from continuing to play in this fashion, and hope to add further insight as it comes.