He is a realtor that I previously purchased a small portfolio from and therefore had a good professional relationship.

So, I am not a "professional wholesaler". 

This person may actually be a licensed lawyer or a real estate professional.

But the only strategic thing about them is that you need to keep good records and hire a tax professional who knows how to maximize the tax savings from things you already paid for. 

I understand this may prevent me from getting the absolute best terms on a HML, so I'll turn to professional before I settle on a lender, but I'd like to start the shopping process on my own.

Readers should seek professional advice.

I went through it anyway bc she had a good footprint online, I liked the designs, and a couple of ppl at another STR group recommended her (not an excuse, I was super busy and thought I was dealing with a professional).

Definitely not what I would expect from someone who is a professional.

On the other hand, true private lenders are not professional lenders and hedge fund type lenders (which is what hard money lenders are), but instead are regular people in your circle and sphere of influence.

Readers should seek professional advice.