These are professionals with additional training and a stricter code of ethics.

The 4.5 approx acres next door would be an additional cost (not owned by me at the moment.

SummitCapital link to their site

I expect that I'll be reserving time in various resorts and farming those weeks out to perspective vacationers, does anyone know if VRBO, or AirBnB, or some other site would be most appropriate for this approach?

There will be someone from PadSplit on the call to help answer additional questions you may have.

I just bought a new property and I was wondering if I was going to rent this out, what repairs should I make in terms of the roof and should I add an addition?

Not officially but they are on the site.

Additionally, consider negotiating the ability to delay or cancel some bookings to complete the necessary work sooner, avoiding further damage.

Thanks for this clarification Bill.Let me add a bit more context and see if anyone can chime in with additional advice. 

I do this actively networking with other investors, sharing content on sites like Bigger Pockets and Think Realty magazine, and building relationships with referral partners like wealth managers.Finally, you have to have the best people working with you from your lender partner, to your property inspector, to your property manager, to your insurance partner, and asset protection and business attorney.