My main pro for it, is that at my income level, I think paying corporate taxes for the rental income with a C corporation would be less than paying it as pass through income i.e. personal income tax. 

@George Vigil I don't think I'm qualified to provide the level of feedback between the options or the market.

It should be something like $600-$900 for the first year depending on the level of coverage you choose. 

While its possible that it might go through I would rather assume the worst-case, especially because I don't want to take on that level of risk. 

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.