As Marcel pointed out, the key is to add your plugin as part of the solution. However, I do want to point out that most plugin projects will likely depend on the SmartStore.Web project, so that being the case you won't be able to set the plugin as a dependency of the Web project (VS will warn about circular reference). As such, it is important that you manually build the plugin and make sure its build output goes into the Plugins folder of the Web project (see other plugin project build settings on how to do this) before every debug run. Once your plugin files are correctly copied or updated, run the Web project in Debug mode and you will see your plugin being already available for install - no upload is necessary. Hope this clarifies.
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