Since I have never done a deal, I'm not confident enough to do things on my own.I'm looking for some recommendations on coaching programs.

If the agent you work with is not familiar make sure the lender is, so you have someone who can confidently navigate this path for you.

I'm confident if the Bomberos were not already on site the entire campo including our property would have burned down. 

Find a valuable agent to list them, or work with @Dave Foster to 1031 properties, and you'll be less stressed. 

After talking to my accountant we feel confident we meet the requirements.

The data points they use made me feel like it got my pricing right and I feel much more confident about what my nightly and seasonal rates are now. 

@Dave Foster Thanks for your reply!

If you're confident in the flip and have a contingency buffer, a HELOC can work.

If are confident you will receive a permit, then somethings to think about...#1 I would call the city rentals department directly and ask if the seller's license will remain active until the day yours becomes active.

Since you mentioned REI Hub, I worked with REI Hub in the past and they had the same connection issues but their CEO is usually good about making quick updates to create a better user experience.That being said, there is no perfect solution out there regarding bank feed connections so I'd go with one you know and ensure the accounts are linked on a weekly basis to be confident every transaction is flowing through without interruptions.