I think Rafaela needs to be included into our future outfield plans. His defense is amazing, JBJ level and he can do it at CF and at SS. If he an at least be an average hitter that's going to be a tremendously valuable guy. With the new rule changes, up the middle position players are going to be as valuable as ever.
The time to go all in, may be next season. I hate to say it, but there's too many holes to fix, it might take a cleaner bill of health and luck to go all the way next year but I think it's reasonable to assume they should compete.
I also want to see how this young pitching pans out. Having a clearer picture of what guys like Houck, Whitlock, Bellow, Crawford, Mata and others can provide and what roles they may play will make investing in closing the gaps that much easier.