How to make things easier? Good question... Warning: rambling post ahead.
The majority of my listening is divided between home systems and mobile listening (i.e. from my laptop). For that reason I have effectively two collections. I can't rely fully on a NAS plus streaming, I also need (and appreciate) the collection on my hard disk (and streaming capabilities of my laptop). CD's I play only at home.
I think what I miss most is an easy way to use my laptop as music centre at various places. Presently I work principally from Audirvana, which nowadays integrates streaming: a big help. But the external connectivity means that I change between several (portable) DACs, amplifiers and speaker systems at various places (work office, home office, public transport, kitchen). I don't like Bluetooth, so that is no solution. At present getting the music I want means first spending several minutes setting up everything (turning on stuff, connecting USB, selecting DAC, selecting source, selecting music). That's not problematic but it would be nice if it could be made easier.
Also I would like the possibility of DSD playback in my living room system. This would now require a different streamer and possibly an additional DAC. Although I like the Bluesound Node (particularly the apps) I am considering going the Raspberry Pi route for this reason. I'm hesitant about all-in-one solutions as I've found I like to upgrade single components when new possibilities open up.
Put differently: it's somewhat irritating that all systems have different capabilities and interfaces. To make this uniform, however, would lock me into a single eco-system which I don't want. For the same reason I don't like a multiroom system, even though Bluesound offers this as a possibility.
Furthermore the software side might conceivable be improved. I've heard good things about Roon but that is quite expensive and might not work for me; the seamless integration of various sources and formats sounds appealling, though. On the whole, however, Audirvana is really nice and would be even better if it would help me cope with a variety of interfaces/sources/DACs.
Finally, I don't like start-up delays, which most systems seem to have. I'm continually surprised that fast computers don't lead to fast booting up.