Now your comment made me realize of someone at Type/moon (Fate Stay/Night) could end up making waifu versions of Hitler and JFK eventually given the series tendency of doing this with historical figures.
The Fate series doesn't change all into waifus(thankfully), as there were people who wanted Napoleon to be a small Waifu, but when Napoleon got in, he stayed a man(and was actually normal sized, although it was implied he would become the short one if he was a different class).
As for those two in general, it will probably be either a very very long time or never due to controversy. As much as Fate has fun with older characters and doing some twisting to make said older characters more sympathetic or less of a ****(in
most cases), they still keep tabs on possible controversy. Possibly the reason why Toyotomi Hideyoshi hasn't appeared in Grand Order yet, as while he does appear in one of their gag mangas, Grand Order is also played in Korea and Korea has a real beef with him still.