Im using several windows services in an ongoing project. They have worked out very well. I choose the services approach for many of the reasons you mention . I’ve also found that this option can have a great deal of flexibility. In our environment the folks at server management tend to be busy and cant always respond to request in a short timeframe. With the windows service I was able to use sql server to configure parts of the service on the fly. Things like suspend service, service status messages detail , how often the timer would poll for import file could be set on the fly without having to contact server management.