So I'm in the market for a new broker/agent and a new insurance company for at least one building and possibly more. 

Highlight the cash flow and equity in your property when negotiating with lenders, as this reduces their perceived risk.Ultimately, you may need to reach out to multiple lenders or brokers who specialize in DSCR loans to find one willing to take a second position.

In addition to state and local licensing fees, what broker will hold your license for free?

I just passed my real estate broker's license and am ready to hang my license in Colorado .

I've found even though you can get some modest discounts it makes things much easier to keep everything with the broker.

It's all the real estate agents, brokers and other vendors servicing landlords talking about how great it is. 

Not sure what state you intend to get licensed in to start, but before you get too far along I would check with the Real Estate Commission to confirm that your end-game (AI decisions only, no human broker in the loop) will pass their muster.

I found my insurance broker, Steadily, through a BP podcast ad, I found Baselane to use for banking through a forums ad, I found RentRedi which I've used as my PM software for years as a sponsored post.

Call a local broker on the telephone and ask that question.

Boutique brokers can work nation wide also.