Prior to doing so, I have to map my expense items in the chart of accounts, to those in the schedule E at tax time.

It would be like trying to have a baby eat steak and potatoes.Just start off with what you can handle for now.If you do new , do not compete with a property where you can here hammers.Don't compete with the "Big Boys".   

This way, you have a cake and eat it, too.

Ever since DMZ released text messages where actor Armie Hammer details cannibalistic desires with drinking his ex-girlfriend’s blood and eating her ribs, the actor’s career has been in free fall.

If that means renting, eating out less and networking as much as possible on BP. 

If still 'yes' move to c. an ask what premium do you expect the seller to give you (i.e: discount) to make it worth your while should summer comes and you find out that not only you have 10,000's of non-paying residents in the house but that those are literally eating into your equity...Get expert advice on this from people who specialize in termites - both on risk, damage, feasibility of containment and cost of repairs. 

With 400 rentals and over 50% of them pet-friendly, I rarely have an animal cause so much damage that the deposit doesn't cover it.

I would not approve it.However, if the visitor has a service animal, or emotional support animal, that is a different situation.

I'll have to eat.

My guess is they know something is wrong with the unit and they know if you see it it will eat the deposit.