There were some issues - again not with the simple update itself and not even with the program itself but rather with how MSI works on a Windows computer. In the end we had to make some changes how Host installation works. Now Simple update should work ok when updating Hosts 220.127.116.11 to 18.104.22.168. However, these fixes do not work restrospectively, i.e. if you use Simple update to update your 22.214.171.124 Hosts there may still be issues.
However, even if you use Remote install tool or even manual update you don't have to build a custom installer just for the purpose of updating. Use the vanilla Host installer - in this case it will update the program files and leave your settings intact.