Finding good cash flowing deals are damn near impossible.

One of the constants that I still see from when I first started on BP in early 2016 is the willingness of experienced ( some on this very thread ) folks in different aspects of real estate to try and help newbies and others with advice and perspective.I think it really is a testament to the fact that even though the investing environment has undergone many changes over those years the willingness to continue to help others has not changed.It helped me tremendously when I had to crash course on small MF ownership and I am grateful to all who helped with posts that they didn't even know that I had read and learned from.And yes the search function remains fairly useless and unchanged in that regard since then to the detriment of us all.

The vehicle is over 6000 pounds GVWR and will be used nearly entirely for business (going to current rental and searching for new properties to acquire)."

I do not expect at least in FL that regulation will get bad enough to make STR impossible or even nearly impossible. 

My mom is nearing the end of her life and has left me and my two brothers her condo in Hawaii.

A friend of my wife’s brother in Maui has a 5th generation cork and cattle farm near Gibraltar, Spain.  

Near the 56 is a great place to live.

I have couple of STRs near Niagara Falls.

My question is, do I just use the heavily reduced price I was able to purchase it for since it was vacant, and then the material cost of what I renovated plus what things I did contract out, even though that basis would be way under what the other renovated houses that sold near me per SF sold at, or are you able to use similar comps to determine the depreciation basis?

[Because after all that - you haven't paid off your primary anyway, and won't in the near future!]