Rules for downtime activities

In one of his Running the Game videos, Matt Colville describes allowing his players to use downtime between sessions to pursue various goals their character may have. Matt would run one-on-one sessions where his players would work towards these goals. 

Although I found this idea to be very compelling, I was never able to put it into practice. Planning these downtime sessions seemed like an enormous amount of work with only one player getting to enjoy the content. More importantly, I got the sense that my players didn’t know what would be viable goals to pursue. It was too open ended.

Later on, I came across a reddit post that inspired me to create my own rules for downtime activities. In short, players choose one thing to focus on, and they make the appropriate roll to determine how successful they are. The DM then describes the result, sometimes after taking some time to prep or think about what outcome makes sense.

I’ve noticed several benefits from implementing this system:

• The list of potential downtime activities helps players (especially newer ones) decide what they want to do. Most players engaged with the system and had fun during downtime.
• You can see what’s important to your players by what they spend downtime doing. 
• At the start of each session, each player can have a cool moment describing what their character did since the last session.

List of potential downtime activities (not an exhaustive list):

Can do for free:

• Short / long rest
• Sell any non-magical weapons / armor / equipment (for half the price listed in PHB)
• Purchase any non-magical weapons / armor / equipment
• Check the town notice board
• Check calendar for upcoming events

Full downtime activities:

• Ask around for side quests (persuasion)
• Find a job (investigation / persuasion)
• Earn money performing (performance)
• Listen / ask around for rumors (perception / persuasion)
• Ask around for information on something or someone (persuasion)
• Investigate a question / plot thread (investigation)
• Look around for hidden passages / areas (investigation)
• Find a contact for something (persuasion)
• Research something (history / investigation)
• Look for specific magic / rare items for sale (investigation)
• Find buyer for magic items / valuables (investigation / persuasion)
• Rob / pickpocket (slight of hand / intimidation)
• Repair / craft items (requires specific tools & components) 

Let me know what downtime systems you've implemented and what's worked for you!