The executor also has 2 other siblings and they are to split the proceeds of the sale between the 3 of them.

If seller financing is out, agree on a price that will enable the landlord to pay the $30k assessment out of your sale proceeds. 

We do need to proceed with these repairs.

And then you can proceed with the refi.

I would like to get members opinion on these, the overall potential deal and how best to proceed.

If you are doing the leg work (finding the property, negotiating, writing up contracts, inspections, etc) as the agent, I would be inclined to proceed with receiving the commission as the agent. 

It's just part of me just wants to proceed more cautiously.  

If raising rent is not possible, and buying better deals is not possible in your market, I would probably be looking to go in the other direction - divest myself of the rental, hold the primary note-free home, and reinvest some of the rental house proceeds into a reasonable growth mutual fund or similar, and some of the proceeds into something more solid.

I'm not bashful, nor am I arrogant.  

I don't really have a real estate agent I work in the area (the purchase was negotiated directly with the seller), and I'm not entirely sure how to proceed.