Another way to protect yourself from potential liabilities is to ensure you have a bank account open solely for your real estate investments.

(I lived there temporarily on a blow up mattress to ensure all work was completed and managed as the house was an hour away from mine.)

Only other recommendation would be to work with the same lender or broker for both deals because the paperwork is going to be the same and it will make it more efficient than you trying to coordinate with 2 different lenders.  

It remains however I want to ensure the happiness of my friends and family as well.

Each letter is professionaly written with proper salutation, etc.While direct mail works, it is probably the most-expensive advertising and not very efficient.

How have you all structured your cleanings and ensured that you have someone after every booking?

Talk to your CPA and set aside any funds you may need for taxes.Given that you will have zero cash flow over the next 12 months, there is extra burden on you to ensure you are smart with the money and keep reserves in the event there is a problem (e.g.

He wants to ensure that if I make a mistake, we're still okay and I respect that. 

Ensure you get really good with analysis.

You have to remind him that the deposit is your leverage to ensure he complies with the terms of the lease.