So no tangible benefit there.The one exception I would outline is if you want to pool money with someone else and invest together.

Should we just collect a little extra each month until they have submitted the full last month's rent (and of course have the specific payments and what they're for outlined in the lease)? 

The strategy outlined in the book One Rental At A Time that you mentioned would likely be easier to achieve in the U.S.

- Based on my outline above, can you find any flaws in my plan?

It was outlined with penalties on me, recourse, obligations on me, and if I chose to sell, they'd get a % of the sale. 2) Use an Attorney - Here's where I'm kicking myself in the leg.

Prior to closing get an estoppel letter from the tenants outlining the lease terms, deposits, verbal agreements.

I can't thank you enough for the outline - This was fantastic.  

Would you be open to sharing the excel outline?

As I'm sure you know, it's important you view your tenants as business transactions- make expectations clear, and outline everything in your agreement they will be responsible for and penalties if they do not hold their end up.I agree if you ask for too much, they may pass- but it's unlikely (as long as your asks are reasonable), considering the eagerness and need from renters- and they are used to providing most of this with other managers and landlords.

The way you've outlined the opportunity, I would run away from it.