It’s tempting, but not always profitable.Tip: Stick to improvements that will boost value based on the neighborhood, and avoid unnecessary upgrades.Buyer Preferences: Sometimes, the design or finishes you chose don't match what buyers in that market are looking for.

However, failing to pay the tax could result in a lien against my company, complicating the approval process for a mortgage and incurring an estimated $10K in penalties. 

However, failing to pay the tax could result in a lien against my company, complicating the approval process for a mortgage and incurring an estimated $10K in penalties.

Either way, the accountant can pull this easily from the closing statement or 1098 from your lender.It's really not as complicated as you think. 

Unnecessary?

You will also have to factor in rental days vs. personal use days.This is very complicated.

But it will be complicated by different factors such as flood zone, topology, conservation area, easements, access to roads and more.Zoning - check the code and check site zoning.

My question would be, is this a good idea, or am I creating unnecessary complexity in the business structure? 

This is a good, yet complicated deal.  

We tend to complicate real estate...it's as easy as "Would it be cool to live here?"