Make sure your landlord insurance lists the pool.I though about how I would handle this as we have an inground pool.I think I would have mandatory pool service that they pay in addition to rent. 

If you are a professional and legal Property Manager (which you should be) then you should have book keepers and a CPA who handle this for you.

So essentially equivalent to a 50 unit apartment, thus handling due diligence in a similar way.

Ask for someone who handles white collar or economic crimes.

No one knows your stress level you can handle or want to handle but you.

As an agent, I handled all the negotiations and paperwork regarding the offer and the post closing occupancy.

Would I need to have a loan servicing company handle the payments for me if there was no mortgage on the property?

Most of the landlords that I know around me that do something similar to what you're talking about find a good handyman that they can just send their issues to when they arise and then just handle everything else.Just some of my thoughts!

In most circumstances for single family homes, the investor/owner will require the tenant to handle landscaping and snow removal. 

But we are taking possession of the house this week and we will not receive rent this month since it has already been paid to the current seller.How is this situation typically handled?