(This should be cheaper because no personal items are insured.) and then insist the tenant’s get renter’s insurance.

ive been using turbotenant which is cheaper but definitely clunky

I began to track my hours and where those hours went.My understanding is that I can use the STR loophole to reduce my wife's taxable income.

Though it is over 50% cheaper

It may be cheaper in $$$ but it will cost you way more in time and effort.

One of the cheaper shed doors needs replacing…However, it’s a dream house in a dream area (25 minutes to dodge ridge ski resort) and was our dream home because of how perfect it was for us at the time.

Your debt you are taking out does not incur any taxable event, so using that capital for your purposes is wise if you want to keep the asset the debt is held against, assuming your getting a better rate of return then if you didn't have the debt. 

.- Look for off-market deals that are much cheaper.

Those fee should be standard across the board and be the same or very close to the same for whatever you build.Next you need to understand that usually the larger the property the cheaper it gets per SQFT.  

Probably would be cheaper to just hire a PM but may be an option worth looking into.