Hopefully there are twins in your DH's family. That would give you the best chance.

I actually think to concieve twins naturally fraternals run in the mothers side & identicals are a fluke.
To concieve fraternal twins you need to produce two eggs, & I'm pretty sure thats a genetic thing.
Because Identicals are one egg splitting, it can happen anywhere, to anyone.
Fertility drugs are to make a woman more fertile by releaasing more eggs - or trying to. Thats how they often end up with multiples.

But as others have said, there is still a chance that one baby could be lost at the start.
Plus the higher risks to both the babies & yourself.
Also a good chance of having to have a c/s - not always. But imagine trying to deal with 5 kids after a ceaser?
Then there's your medical history. I really think it'd be a big risk to take. You have alot to consider.