I learn with a Rosh Kollel and he refuses to let me pay him. Sometimes I’m able to convince him to take cash. I know he can use the money- am I able to use Maaser to give him money for learning with me?
Yes you definitely can give him the money, and even if he doesn’t want to take it for his learning with you, you can give it to him simply because he needs the money. If he doesn’t want to take the money straight, you can try and fool him into taking it. Say it is a loan, and then a month later say that you don’t want the money back. Alternatively, you can get him the money through other people who he might be more willing to accept from them. Sometimes we have to be a bit creative when gving tzedakah in order to give ot the poor person, especially if he will be embarrassed to take the money straight.
Shulchan Aruch Y:D 253-9.