For someone who has not used a DSO before, who does not yet know all of the possibilities - who doesn't know how much he or she doesn't know! - would the UI of the Rigol (or of the Siglent) be more likely to help this person find / figure out these possibilities? Or does the person really need to learn what capabilities to look for, before trying to find them in the UI?
With both scopes, using the basic CRO-type functionality is easily figured out without a manual. They both have the familiar vertical, horizontal, and trigger controls.
For the DSO-specific functionality, I would say that you will have an easier start with the Rigol: You will be able to figure many things out without a manual because the settings are right there in the dialog -- and if you can't figure them out, seeing them will at least prompt you to look for them in the manual. It is easier to overlook some settings initially in the Siglent, or you might intitially struggle to remember where to find them.
Two caveats:
(a) Not everything is self-explanatory, even with the Rigol, if you have not used DSOs before. You will need to read the manual for some functionality, especially for things CROs can't do, where you may not even be aware that DSOs offer them.
(b) Some of the simplified operation of the Rigol comes at the cost of having less flexibility. The Rigol simply does not offer some options and settings which the Siglent gives you -- making things easier initially, but at a later stage you might wish for some of the extra control the Siglent offers.