In the past, I had some issues with running the wallet on a VM but was able to fix it manually. Going on, will future updates address this? Also, I wonder if there will be a better process for wallet updates in case of another major change to the blockchain? Just asking because for mainstream adoption, things need to be as easy as possible

cryptonight wallets are a bit heavy and clunky. but that has already been discussed. they are focusing on releasing the VPN 1st before anything but im sure they are already thinking about the next step. for the mean time you can always use a remote node from HV and other pools as well.