The Hallowed Hollow
I thought it might be fun to come up with some mechanics and benefits for inn the owned by Orianna. (This is somewhat inspired by MCDM's Strongholds & Followers book) The Hallowed Hollow has a level, and if you chose to upgrade it, it will accumulate more features and benefits.
The Hallowed Hollow is currently Level 1 and it can be upgraded to level 5. At level 0, the inn is roughly breaking even; the inn earns enough money that it is well stocked and staff is being paid. You can get rations for free from it, so if you are travelling away from Lastfort for, say, 2 weeks, you can simply assume you're brining enough provisions for the trip. As well, so long as the party is staying at the Hollow, I won't charge you the lifestyle fees as per the PHB.
Each upgrade costs 100GP * the new level, so upgrading it to level 1 costs 100GP, going from Level 1 to Level 2 requires 200GP, etc. This represents a combination of renovations, upgrades, getting in higher quality stock, etc. Each renovation will take about a week.
Gathering Intel
Once the inn is upgraded to level 1, it gains the ability to Gather Intel. Essentially, you may seek information about a local person, event, etc. To make a Gather Intel check, you decide what you want to seek info about and then roll a skill check with the modifier of Orianna's proficiency bonus. Instead of adding an ability modifier, you can spend gold to improve your roll by up to the inn's level, at 100GP per level. Ie., if the inn is currently level 3, when you Gather Intel you can spend up to 300GP to add up to an additional +3 to the check. You need to spend at least 100GP to perform a Gather Intel check. The DC will be set by me and depends of course on how difficult the information you are seeking is to come across. If you want to know why the local farmers haven't been grazing their cattle in Stormwatch Valley, that's probably a fairly low DC. If you are trying to find out who is actually running the Assassin's Guild in Trinsic, that will be more difficult.
This represents having the staff listen for rumours, perhaps offer some free drinks to the more loose-lipped townsfolk, etc.
Gathering Intel doesn't replace the characters doing their own investigations or speaking to their own contacts, but it's another resource available to you.
Other Benefits
Once the Hallowed Hollow is level 1, it begins to turn a profit. For each in-game week, it earns d20/level GP. So once it is level 5, it will be earning 5d20 gold each week.
In addition, completing a long rest at the Hallowed Hollow has the following benefits:
| Level | Benefit |
|---|---|
| 1 | After a long rest, all spent hit dice are recovered, instead of just half used hit dice. |
| 2 | After a long rest, the character gains 5 Temp HP/Inn Level. These last until used or until the next long rest. |
| 3 | After a long rest, all levels of exhaustion are removed. In addition, spell casters completing a week of downtime at the Hallowed Hollow may swap one cantrip for another cantrip on their class's spell list at a cost of 50GP (this represents the cost of research, incense for meditation, etc). |
| 4 | After a two-night stay in the inn, the character can remove a negative effect as though Lesser Restoration had been cast on them. |
| 5 | After a week of downtime in the Hallowed Hollow, the character receives a d6 inspiration dice that lasts until used. The character may have only one of these dice at a time. |
These benefits are cumulative.
Note: these are my initial ideas and I might tweak them as the campaign progresses.