You are likely to find the cold shoulder from the seller as that is an unrealistic offer -- but do it anyway to prove the Realtor right. 

@Bianca Navalta That is fantastic, you have a really good head on your shoulders!

I have successfully completed 4 properties with gains on each, and am looking to gear this structure into a business entity so that the tax burden is less cumbersome and liability is lifted off my shoulders a bit as an individual.

@Bradley Post Sounds like you have a good head on your shoulders!

You would be very wise to seek out counsel from a competent professional about all these questions.Regarding taxes: I've done several agreements before where we specifically lay out who will be shouldering the costs of taxes and we put a dollar figure on it ahead of time after running calculations. 

I am embarrassed to ask this, but feel lost in almost a loop of analysis where both "A" and "B" answers seem to be the right one depending on the day of the week and phase of the moon.If any of your more educated souls wouldn't mind looking over my shoulder on this one and let me know what you think, I would appreciate it.Ultimate Question: Factoring out significant appreciation, would it be better to pay off a single-family-home rental than finance and buy another one?

My guess is the larger investors who can shoulder increased risk will be the ones who benefit most. 

It would make less money sense, but it would be nice to use it myself when family comes and on the shoulder season weekends.

So they're going to do the same job they would do anyway, but you get to pay as you go AND shoulder the risk of long-term vacancy, unexpected rehab issues, etc.

But with 11 units in 5 buildings, it looks like to me that you're planning on shouldering what will likely be a massive burden.If you're dead set against hiring a professional management company, even for the first year, I can understand.