I have had several interesting conversations with other investors on the importance or lack thereof finding a good lawyer when establishing an LLC. 

That’s probably your best bet, avoiding a direct conversation with a lawyer about the issue and just motivating the client.

I've had great interactions with contractors only to end a conversation by saying "you're rate is more than a doctor, and I'm an investor..."

I’d start just by introducing yourself and having a low-key conversation about what she’s thinking of doing, what your plans in RE are, and see if there might be a match.

Unfortunately I’m learning that I should have had my conversations with the tenants in writing.

I asked her what 'other issues' need to be addressed and she responded by accusing me of being 'verbally abusive' with my 'tone' (via text conversation) and that I was inappropriately 'badgering' her to tell me *now* what she wanted to discuss requiring a house meeting. 

You can also have a conversation with her offering her the option of leaving on her own.

If it turns out after that conversation you do need private money, then well at least you know what you are working with.  

One advice is connect with a professional and have a conversation along with your CPA or accountant and see the best path for you regarding your options.

In this case, however, it’s important to me to leave them feeling good about our conversation.