^^^ Thank you for your input. I sent an e-mail to our local DPE, he suggested that I tell the student get a FAA medical to prove intent of flight instruction.

Still checking on the "supervised solo" requirement for private pilot certificates in a twin.

Does anyone have the 14 CFR regulation for "Part 61 allows "supervised solo" in a ME airplane for commercial pilot applicants"? The only thing that I found was...
14 CFR 61.129 (b)(4) - 10 hours of solo flight time in a multiengine airplane or 10 hours of flight time performing the duties of pilot in command in a multiengine airplane with an authorized instructor (either of which may be credited towards the flight time requirement in paragraph (b)(2) of this section), on the areas of operation listed in §61.127(b)(2) of this part...