First let me say I’m super excited to be a part of the wayfarer community! I’ve been playing off and on since 2016 and it’s even one of the main ways myself and some of my family stay in communication.
I have a few questions, forgive me if it’s covered elsewhere, I’m asking because the information did not stick.
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If a pokestop is no longer valid - ie: an intended to be permanent sign was smashed by a car and no longer exists, but the pokestop still shows the sign and location, does it need to be removed?
— idk if they plan on rebuilding the sign, from the looks of it probably not. I assume the name on the sign likely has long since found other ways to donate resources to the community, so they may not be interested in replacing it.
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Is there a way to add supplemental images to existing pokestops? My city recently installed huge Mexican Art pieces that are really cool and many are located at existing pokestops, since some of the stops have multiple images, would it not make sense to include the art installations?
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There are several electrical boxes around town that have been painted with some form of a mural. These boxes are also existing pokestops, I noticed many of them have recently been repainted with new designs.
Does this mean they need to be removed?
Would it not make sense to submit a photo of the new design as a supplemental item?
- that way the old design is still saved, but the new designs are able to continue being added since the boxes themselves are permanently in place.
I learn better via discussions and asking questions, so again if it’s something I missed in existing resources, I would appreciate help via discussion instead.
There are some odd rules about what is considered repurposing and when a waypoint should just be removed and replaced. It seems like business changes should be replaced but art can potentially be repurposed? What is considered to be Repurposing?
Welcome to the forum 
If the POI for a wayspot no longer exists, you can report it for removal. This can be done in Pokemon Go through the three-dots menu or on the wayfarer map at Niantic Wayfarer.
Additional images can be submitted for wayspots through Pokemon Go or through the wayfarer map.
Murals, such as the ones on electrical boxes, are generally immune to the problem of repurposing (when the POI changes and becomes something else, such as a shop being taken over or a playground being rebuilt). The normal thing to do is submit new photos.
#2 There are existing pokestops at the location. What are they for? Are they for the art pieces or for something else that exists nearby? Never add photos of something else to an unrelated waypoint.
#3 this sounds like a good opportunity to add a new photo then just edit the title and description.
These are the photos I took of one of the art pieces in front of the Steinbeck Museum. There is already a PokeStop for the Museum..
My additional images were denied as soon as I posted them today. So 
The other one I mentioned, rose bushes have been put in place of the smashed sign I think it’s safe to say they won’t be replacing it.
These are the photos currently in place at the same location
Hi and welcome, thanks for asking since there are indeed some rules around this!
The photo of the coyote is fantastically pretty but it is not a photo of the museum. As suggested above, it’s not okay to add photos of a different object than what the wayspot is for. There is probably a way to take a photo of the museum with the sculpture in frame, but it still has to be a clear and unambiguous picture of the building the wayspot is for. So it’s normal that this got rejected.
If there are other interesting and separately eligible objects nearby, then they can be submitted as separate wayspots and that’s the best thing to do if you see other stuff you like in the area (just check that they are not already in the database first). It will however not be possible with this artwork since this is a traveling exhibit and is due to be removed on September 4th, from what I’m seeing. https://www.instagram.com/p/Dbe8tkQEx6f/