TLDR
If you have a sketchy or low data-cap connection enable your Rolling Cache (RC) for those offline days.
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All this time I kept wondering what the fuss was over the RC. Now I get it. Due to a change in circumstances I lost the high speed unlimited internet at my place (a housemate whose account it was has moved out).
So I am now using my cellphone via USB tethering to my PC to get internet. But the data cap is 10GB/month which of course is joke-level for MSFS.
So I fly with Bing Data turned off and the sim looks AWFUL .
Modded FSX looks better than Offline MSFS without a doubt.
So yea - if you have a favorite place you keep flying in make sure your RC is on so if you face a similar situation (which is rare for many I know) at least you can enjoy the Bing data eye candy in that region with Data turned off!
Remember that at some point (e.g. depending upon the size of the cache) the data stored in the Rolling Cache will be overwritten with new data as you fly away from the original location.
If you want data for a particular area to persist, irrespective of where you fly, it would be better to use the Manual Cache.
A different scenario indeed, but following SU15 I have been running a 16GB RC and my Series X seems to very much like it. Of course I purge it after any minor update comes along and after buying stuff, just to be sure, but will leave it as part of my configuration and leave behind all the old arguments for leaving it off. We had a MOMENT during beta testing for SU15 where the RC really shown but had to be pulled from the release candidate for more refinement of the underlying GDK (another topic really) and that moment showed me what a RC can do for MSFS. Anyway, others may disagree but the RC is here to stay for me until something breaks it!