I'm a little leary to think that 6 nights (3 weeks * 2 nights) is going to be enough to cover mortgage, insurance, property tax, maintenance, cleaning, furnishing, 100% of utilities, cable, internet, etc. but maybe I'm all wrong. 

The way he arranged it might have even included some other mechanisms but I can't remember (life insurance, ira, annuity?)... 

.$3,000 in escrow for taxes and home insurance.Monthly payment will be $1,375 which includes taxes and insurance figured in.The monthly rent is $1,650 so that will leave me a cash flow of $275.To remind everybody this is a SFH that I purchased 2 months ago and should be appraised at around $210,000.

The one property we took back (DILO) cost us about $9,000 for a new water line as we didn't yet have it insured & we already had an offer.

I'm very reluctant to give in, its nice knowing if for whatever reason we can't re-rent, the current tenant has to meet their contractual rent obligations. 

Insurance is about $70, and there are no property taxes for a property under 75k in Louisiana, property management of $65.Rent increases about $30-$50 a year.I'm looking to cash flow about $215.

In that case, certainly get the seller to sort that out first or you could have a headache.The property management company that I like and trust never hold you to such obligations from the start, they operate with the highest quality of service and basically maintain that if you don't like them you don't need to work with them.

Can anyone offer any advice on lease structure and insurance requirements to get this started off on the right foot to allow for a win-win for all involved?

Financing and insurance were first up.

Option 1: One mortgage, both on it, you're coborrowers, no different in terms of responsibility/obligations/etc than an engaged couple buying together.Option 2: One mortgage, only one person on it, the other person can be property manager or whatever you work out once you own it.Option 3: One person on mortgage, both on title.