Hi, my name is*****'m a certified appraiser, and I'd be happy to help.
This bank was patented in 1883, but was not actually produced until 1907, by the J&E Stevens Company in Cromwell, Connecticut.
Yours appears to have all the original feathers, which is excellent, but it also appears to be repainted, which isn't so good.
An example with original paint in good condition would sell at auction in the $4000 - $5000 range. Repainted, it would probably be closer to $1000 - $1500.
Please let me know how I can help further.
On the Indian, you can see how at one point the headdress feathers deteriorated, but the paint over them is very clean and fresh--so it's clear it was repainted after that point. However, given it was made in 1907, it could have been repainted in 1920 or 1930 or some other time before your dad saw it. It was a pretty common item when it was made, so certainly would not have been in a glass case as a memorabilia item until much later.
Regarding the token, Hitler was often compared to a pig--there is a famous and collectible piggy bank that has Hitler's hair and moustache. There were also many propaganda fliers and posters that compared Hitler to a pig. That said, I've never seen this little piece before, and I'm unable to find anything specific on it. The value would be around $75-$100.
I see this question is still open. Can I help you further?