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Is it typical for firms to expect JD only tax associates to do a part-time LLM, and/or is it typical for firms to pay for the LLM?

Practice & policy probably varies by firm.

Based on research that I have done on Wash DC law firms, many resumes/CVs show that a Georgetown LLM was earned on a part-time basis over three years while working at that firm. This suggests employer sponsorship.

I think the practice and policy even depends within a firm. At my firm probably 50% of the tax associates have LLMs, but some sub-groups won't hire folks without an LLM, some ask associates to get an LLM part time, and others just don't care. I think it comes down to the preferences of the partners.