2 CRE Networking Questions

Contextual Info: On August 24 of this year, I made a post asking for advice for how a very social, former college athlete with lots of drive, math/econ/speaking knowledge, but no experience could carve out a place in a finance field. Since that post, one area I have been looking into is the commercial realestate sector. So far I have REFM levels 1-3 almost complete, and I have started the ARGUS certification since I have the funds to do so. However, my work experience, especially in the field is very low.

2 Question: 

1. Is it appropriate to ask a VP of Global Realestate/ Facilities at a top 10 company in the US (when ranked by market cap) to do some sort of free work so that I can at least put something under work experience? In addition to their job, this person has a large personal real estate portfolio so I assume there is something regarding those properties that I can offer to do for this person. I also have the advantage of a close relationship with this person (I was best friends with their son in High School and we still hang out today) so I feel like I could ask this in a way that comes off well rather than needy or entitled. 

2. Am I just overthinking this and should just text this person?

Reasoning: While I do not expect to work for this person's company through asking this person, I'm sure they have their own internship program because I've already applied to it, I think that a good reference from a well-respected profession, along with the work experience could help me get a real internship sooner, rather than later. 

Thanks in advance for any feedback!