All-in I would have like 20-25k saved up, assuming you don't pay agent fees and can find a lender that will float you the first chunk of construction money. 

Lived in upstairs unit for 3 years, then rented both units out for the next 12 or so years Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I'd recommend you start with reaching out to successful agents in the area and asking their opinion on where people like to invest.

Currently the plan is to use a lawyer the selling agent recommended. 

Why not do Property Management, I see you already are a licensed RE agent, getting a license through Hotels & Restaurants is not too difficult.

-typically an agent and a PM will not oversee a major rehab. 

This kind of stuff should only happen when you self-manage (or maybe hire someone who’s primarily a real estate agent not an PM.) and would be a good example of why I don’t.

I am a STR focused investor/agent.

Does your agent work for the insurance company or are they independent? 

Being an agent is a job...it is a sales job.