During that time, you manage the tenants, collect the rents, and market the bajeebies out of them and sell off 9 unit at closer to retail so you profit enough that you can keep one for yourself. 

Putting value on our time, we figure we are closer to paying out 3-3.5% and that is well worth it to us for the peace of mind.

Without getting too personal, our parents are north shore people and we want to be closer to them.

This now made Apopka more convenient to Maitland than even living physically closer in Altamonte Springs. 

As a side note, 5% down on a $400k loan would make P&I closer to $2040 rather than $1900, and that doesn't include PMI or taxes.So say you rent out three of the units for $1300 = $3900 monthly income.Now, subtract 50% for expenses and you're left with $1950 as your NOI.Take out your mortgage payments of $2040 = -$90 monthly cash flowSo you'll have negative cash flow based on this very loose evaluation, and assuming you live in one unit.

I would make a cash offer that includes everything you want to fix, an offer of some money now and yearly installment payments; and a monthly cash flow offer that is higher/closer to what they really want.  

I'm thinking maybe in ST.Pete or closer to Tampa would be better year-round, and the beaches for short term, but whats the middle ground place?

What if the tenants think "proper" yard maintenance includes lovely, long, tall, bushy grass?  

Cut grass, weed eat, edge, remove all grass clippings.

To me this looks like an ok deal, but closer to 10% cash on cash