Very smart way of getting into RE investing, congrats!

It will be my first rental which is why I prefer new but is it smart to ignore the rule in this case?

Thinking about tax implications is very smart as it's easy to accidentally create a tax consequence if not done correctly.

Never ever heard of a company paying the lost rents as well like Tim said (unless you bought tenant skip insurance) but who knows lots of companies do lots of different things.I see lots of companies allowing the owner to make the final tenant selection like James mentioned and although it's crazy from a legal standpoint (opens the PM up to discrimination claims) they all do it so if anything goes wrong with the tenant they can fall back on the fact that the owner picked them (which is pretty smart).

I want to make a smart choice.

So whats a good way to really proof read (have help proofing) this plan of mine to find out "holes" or a lack of knowledge placed in any of the areas need to invest with smart choices and minimal loses from the start?

Smart lady!

If they were so smart, they wouldn't need you.

Smart!

My thought was that it would be smart to pay January mortgage payments in December so that I can lock in the deductions for 2016 while tax rates are marginally higher while also locking in the mortgage interest deduction for at least one more month.