Over the years I've gone back and forth with upgrades to analog and digital in my system. For me planned upgrades to either side need to outperform the present superior side. I'm presently at point where it will take $10-20K to bring analog up to or surpass digital.
I've always found analog needs to outperform digital side in order to motivate me to use. My digital side has been at least satisfying for years, and the convenience trumps analog. Digital has gotten all the attention in recent years, reason analog needs major expenditure to catch up.
For vinyl only guys just getting into streaming expenditure will depend on how ambitious analog system is. Reaching too low on digital side will result in disappointment, it really takes quite a large expenditure and paying much attention to every single little detail to reach upper echelon of streaming. Streaming at highest level is complex and so many choices!