I am building a pi-based weather station. I have an outdoor weatherproof enclosure that I needs to have access to two 110V power outlets (one for the pi and another for an anemometer). What I would like to do is install an outdoor-rated surge protector (power strip) inside the enclosure with the power cord running out of the enclosure. This way only a single power cable would run out of the enclosure and multiple devices could be connected to power inside.
I have not had any luck finding examples of this. Ideally I don't want to have to drill a hole in the enclosure that is any larger than the power cord diameter. In order to accomplish that though, I would have to disconnect the power strip from the cord and reconnect it inside the enclosure. Is this common for projects like these?
Are there better commercially available solutions or popular methods for wiring power into an outdoor pi enclosure?