The 2nd level spell Animal Messenger, when used on a flying creature, can send a long-distance message, and if the animal is friendly and well-trained, it can easily carry a small bit of cargo, like a document or a small pouch of coins. Of course, there is a real-world precedent for this in using homing pigeons to send messages.
Unfortunately, when cast at the base level, the messenger can only travel 50 miles, so in order to get the distances you're looking for, it will probably be necessary to cast it using a 3rd or 4th level spell slot, increasing the range by 100 miles for each additional spell level. Alternatively, it wouldn't be impossible to set up relay outposts every 50 miles along the roads between cities where low-level casters are stationed who can cast the spell at 2nd level as a ritual all day long, continually forwarding many messages per day. This would be a bit like a telegraph network.
The main advantage of this approach is that you don't need to acquire any magic items. However, you will need to acquire the services of either several mid-level casters (around 5th to 7th level to cast 3rd-4th level spells) or multiple low-level casters (3rd level to cast 2nd level spells), and you'll need to train a bunch of homing pigeons, which may or may not be easier than acquiring a pile of magic items depending on the setting.
One important limitation to keep in mind is the speed of messages: 50 miles per 24 hours. This means it will take several days to send a message a few hundred miles. This is probably fine for most day-to-day guild business, especially considering that all other mundane communications are similarly limited. However, it may not be ideal for emergencies.