Possible window seat for my guard dog
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I would not use chalk paint - I don't thin it would hold-up. I think the cushion with velcro is a great idea. Sweet dog!
Repaint and take the dimensions to a glass company. Have a nice thick tempered piece of glass custom cut to lay on top of the wood. It will protect the finish and withstand his guard duties!
https://www.pinterest.com/pin/238409374002360110/?lp=true
We have the same type window, but longer and a little narrower, just deep enough for a medium size dog to lie comfortable to watch out the window. We have an old love seat the dogs have taken over underneath the window so that they can watch out the window at the dogs and people going by. We were thinking about putting another piece of wood over the original wood so that they would quit marking up the wood. It is grooved up, but the finish is still intact. A cushion is a good idea, though, perhaps even tile would work.
As for the cushion, I would be concerned that it would slide off with the weight of your dog. I have a 145 pound great dane and There's no way she won't fall off with the cushion moving. Velcro isn't strong enough to hold the weight of your dog with a moving cushion. I personally like the idea of tile, but you could also finish it with hardwood or laminate. Then just put a quarter round trim to cover the rough edge.
How about peel and stick floor tiles. They are easy to cut, and there are so many styles on the market to choose from. Some even have light texture, which will help with the possible slipping concern
If you sew - make a cushion to fit the space and use velco to secure to the wood. If you want to paint again - I would sand it, prime it good with Kilz (2-3 coats), then paint with your choice of latex paint and then use a polycrylic on top to seal.
I would make a cushion and add edge/border half the height of the thickness of the cushion. It will help keep the cushion in-place. For extra security maybe add several small "I" hooks into the lower window trim, add ties to the cushion and use them to ties cushion in-place. Vinyl is slippery. Maybe create a denim fabric slip-cover, washable and certainly comfortable for your furbaby. You can also buy nonslip shelf liner at Dollar Tree and handstitch strips on the bottom side of the cushion.