@b3bowen - Interesting that air layer fail for you. Evergreen Gardenworks sells cutting grown 'Inabe Shidare', and in general, if a maple can be propagated by cuttings, it usually can be air layered. However, the younger the branch used for the air layer, the higher the success rate.
Also, I found long fiber sphagnum wrapped with plastic wrap, has a higher percentage of "taking" over hanging a pot of bonsai potting media in the tree.
@ForThemWhatCare - Some Japanese maples, Acer palmatum - will air layer, some won't. As a general rule, the weeping dissectum types tend to be reluctant, but it is not universal. If you can find a copy of Vertree's book, Japanese Maples, there is a table that lists varieties known at the time the book was written that can be propagated by cuttings or air layers. The book is over a decade old, so newer cultivars are not mentioned.
With the 2 trees in your photos, they are both dissectum types, hence both are unlikely to air layer easily. However, there are dissectum types that DO air layer, though they are a minority. Only way to tell without knowing the cultivar names is to give it a try. Select a branch as your donor that if the air layer fails, will not completely disfigure your landscape tree's value. Hence a smaller branch. Give it a try and see if it air layers.
Success with air layers and cuttings is very much dependent on subtleties of technique and timing. For cuttings, you really need bottom heat and a method for maintaining humidity. For air layers, the age of the branch used for the air layer, and how you set up the air layer, for example sphagnum moss versus perlite, wrapped tight with plastic wrap versus no plastic wrap, rather a pot hanging - all these factors make a difference in whether or not you have success. Various cultivars of Japanese Maples range from being easy to air layer to extremely difficult or impossible to air layer. It is cultivar by cultivar. And technique does matter. So some with better technique will have success with a cultivar, where a "mere mortal" might fail with the same cultivar. The list of cutting grown Japanese maples sold by Evergreen Gardenworks is a good place to start. Those cultivars will potentially air layer if your technique is good. Note that Evergreen does use a professional grade propagation bed, sith heat and humidity controls to do their propagation.