In my experience it mean next to nothing as far as regaining access. No, you do NOT LOSE anything as far as settings or preferences, DVR transfers, etc. even if the 30 day period has passed. I think the limit is 5 devices tied to each Hopper. Yes, each Hopper is counted as a separate of 5 devices.
In my experience, if a device has not been used for Dish Anywhere (and to my experience it has meant just loading the app and being connected to your account and particular Hopper--again with accounts that have 2 Hoppers, each Hopper is granted its own 5 device limt) in the last 30 days, and there is at least one room for one more device to be allowed access (say 4 out of the 5 slots are used, but that ONE is still open) has not been used in the last 30 days, it automatically places that past 30 day device in the place of now authorized devices. There is NO prompt to enter usernames or passwords if you have done so in the past--IN MOST CASES. In fact one of my tablets does NOT have access to wireless networks, only WiFi, so to be certain I can still access my DA DVR transfers, I just LOAD the app at home with access to the internet to reset the tablet's DA access for the next 30 days, and I can view my DVR transfers with no internet connection and with no problem.
However, if all your 5 slots are filled with devices less than 30 days since last use, then you will get a message stating that you have reached your limit of devices on one account, and are advised that if you wish to have the current device access Dish Anywhere, then you must REMOVE at least ONE other device from the list of devices. In this case, you may be required to log on the device to be added after removing one of the other 5 devices from the list.
We have at least 3 devices tied (meaning on the LIST) to one of the Hoppers at all times. However, some of those devices have not accessed Dish Anywhere for as long as a few months, which means they have expired access to DA, but since they are on the list, the moment we load DA from the FireTV or phone or tablet, they will load and automatically gain re-access for the next 30 days with no prompt to log on. Easy Peasy; no work involved.
One way to think of it is that in the case of the limit of 5 devices already on the list, it functions like a revolving door: if one device has passed the 30 day limit, then any OTHER device not on the list will take that expired devices place on the list automatically, I can't recall if you have to log on in that situation even if the device has been logged on before. The only time you have to take an action of removing a device is if you are trying to add a 6th device, and all the other 5 devices are still within their 30 day access period.
Now, that is from personal experience, and Dish may have changed things, since, but it is really pretty hassle free, and even the process of removing a device so that you can have room on the list for a different device is not that big of a deal, either.