I've owned boats (or should I say a boat owned me), tinkered with cars, gone fishing, collected "things" but also avoided golf and in comparison, this is by far the least expensive hobby of all of them.
I'm also retired and I can honestly say that any time spent off my ass and on my feet is a blessing. If people think flipping a boxed machine is going to be a money maker or wash, forget about it. If the cost going in is a problem, there's always credit and if you understand the proper ways to use it later in life, again, this hobby is cheap.
This isn't baseball cards, beanie babies or coins. There isn't yet a large market. There is no large drop anywhere near happening.
About the only way to lose big is to not be able to maintain and do small repairs. If it isn't broken, it isn't pinball.