Thanks @John Warren, I'm trying to play all angles here and am also looking into techniques to extend the life of a deck.

The instructors were phenomenal and made the material much more memorable by providing real-life examples. 

We moved to Wisconsin, mainly motivated by providing a better life for our 1 year old son.

Wanting to have a business of our own and also to have cash flow to supplement our income and life style.

Ultimately though, my end goal is to acquire enough properties so that my passive income is enough to enjoy a modest life and quit my job.Thoughts?

Looking to start investing as a way to generate semi-passive income in order to increase my quality of life and spend some more time with my family. 

Like anything in life- some guests are fantastic people and renew my faith in the STR system as well as humanity, some seem like they are from another planet and have insane expectations.

If you get a cost segregation study though that identifies a significant percentage of the property is actually personal property with a 5, 7, or 15 year life you would be able to depreciate it much faster- perhaps even in the year of purchase with the new accelerated depreciation rules. 

She's had a good life and it will continue at a retirement facility, a few minutes from my house.

Here we go with the "every Property Manager is a lying thief" rants again.Here's how life works.