The lawyers handling the divorce and CPAs need to answer this.

I wanted to ask more experienced landlords how should I have handled this situation.

Those threes are easy and handle 99% of my rental leads. 

Learn your market and get to know your contractors and the work load they can handle and how quickly they can get to your project to help determine your best course of action.

Nothing you can't handle with the BP community and interviewing some of the great people here that are in those areas. 

I know people who've had success with Buildium and I can tell you from personal experience that Appfolio can pretty easily handle a portfolio of several hundred units.

JD also manages a co-hosting company that handles all STR operations for owners.

I strongly recommend meeting with a real estate attorney, and seeing how this can be accomplished correctly;  let them handle the process.    

In your proposed situation, here is what I would do:1) Make sure you have a good/solid/reliable contractor that can actually do the work and has capacity to handle the project.2) Apply for the max HELOC and get it established. 

I'm trying to find a property manager that handles mid-term rentals and will also need help with furnishing the properties.