1) Is it permissible to see istikhara frequently for small tasks to know the will of Allah SWT?

2) Can an istikhara come out good for a task which is not allowed by Sharia? Or a task which is haraam?

1) Please watch this lecture to find detailed answers

https://youtu.be/cuMGgaiIZMo

I don’t advise istikhara for small tasks, only for those you’re really not sure about after using reason as well as consultation.

2) We cannot use istikhara for haram acts. It’s not valid