Maybe if you want people to feel comfortable, make it clear the meeting is for anyone (if it is) no matter what their experience level, and be nice to new people and go talk to awkward looking people in the corner, cuz that's probably me. haha. 

I think it's awkward and I'd prefer tenants not know who I am.

IMHO, the most socialy awkward thing to do is, to inject yourself in a conversation that you were not part of/invited; however, I tabled my social cues and went forward with a business card and politely asked to be apart of the conversation.

If you have liquidity issues now and can't pay him full rate, then pay what you can and offer the rest as a deferred payment once the property sells - it can all be made legal and binding in a short written contract, and while it may seem awkward at first (family member), it sets a precedent for the future when you start doing more deals.

I feel a bit awkward, but I guess it is the price you pay as first timer.

What is a good approach without making it awkward?

(I will be honest, it was very awkward fielding phone calls at first but I’m glad I did!).

But warning: I think we've gotten a little better, so you'll have to put up with a bit more awkwardness!

I was very upset with him for making me have this awkward conversation with him.Point of the story: don't hire your tenants.  

@Ken Walsh this is one of those awkward things you have to deal with being a wholesaler.