If you have a lot of variation, you need a thinner plank (or even a glue-down) to follow the floor's contour or you need to level the floor really well.

Do some research at the local level to find out who can/can't manage STRs in your market (that you don't own).  

Consider creating an LLC - if you’ve not already Ok those are pretty high level - sounds like you are on the right path.

I would just evaluate the exterior in comparison to other recently sold properties to ensure it is on the same level.

So perhaps you structure your payments at an amazing rate such as if they have already achieved 100% occupancy with quality tenants (i.e. 700+ credit scores, or 4X income levels, or 90% without pets, or other such criteria you deem highly valuable) and require cost-sharing for anything that falls below that standard - the "penalty" I was describing above. 

The most important thing to understand about DSTs is that you will need to partner with a firm to do due diligence at the property level.

@Scott Stevens this is outragous on so many levels.

Sometimes, however, if your trading activity is substantial enough, it can rise to the level of "trade or business" which has both positives and negatives.

What kind of people/ careers/ occupations would help stabilize your team and take you to the next level?

I've add others just tell me to look at occupancy, which is a difficult to use at high occupancy levels when I'm looking to add a substantial number of new units to the inventory.