I'm half tempted to try managing it myself for a year but we live two hours away so the logistics of tenant turnover are a concern. 

Let me preface this by saying I am no expert on construction, so I won't be able to give you nearly the same logistical info that the people above have given.

As long as you can later prove that this money did come out of your pocket, no issue.As far as your logistics question, let's flip it and consider it from the buyer's side.

Consider hiring a property manager to handle the logistics if you go STR.

We are looking for a good reputable company can handle all those logistics like maintenance, managing the renters which give us LEAST trouble and a piece of mind.

The custodian will handle the logistics of the roll-over.

From your perspective it's a logistical pain and (to the point of others) what if he doesn't come up with the annual commitment?

Now, let’s dive into the upsides and downsides of moving to this kind of arrangement.The Upsides of Consolidating Your Insurance into One ProgramSimplified ManagementManaging multiple policies with different renewal dates, coverage limits, and terms can be a logistical nightmare.

Basically:-Homework homework homework, know all the project costs, logistics, and numbers and never be optimistic always expect the worst.

And, just logistically, it’s easier to drive by a 100-unit complex than it is 100 SFRs.