Love that you are coming to the market to interface here, nothing can substitute it in my mind.  

If you’re running a MTR more like a STR, then you can decide to charge the full boat as agreed or, if you desire (possibly to obtain a good review) find a substitute renter for the period in question and credit the original renter.If, like me you operate a MTR more like a LTR just for a shorter period of time, you probably use a specific rental form provided by either the state real estate commission of the local NAR affiliate.  

I'm not an expert on that market but there is no substitute for local knowlege and time spent on the ground. 

We use Avail.co to do the background checks, prepare and store leases, and to offer the required renter's insurance policy.Stessa.com does a good enough job acting as a free substitute for Quickbooks.AirBnB and Furnishedfinder.com for listing the space (though I will be trying MiniStays soon). 

I pulled some past deeds and it looks like a substitution of trustee and full reconveyance can be drafted by title.

But that's the nice thing about real estate, money, time and energy are interchangeable, you can substitute one for another.

It's great to ask these questions in the forums to get a feel for things but it's not a substitute for getting "official" advice from an REI-savvy tax pro that you have hired.Regarding what to deduct versus what to capitalize (and depreciate over time), your tax pro can walk you through that for each line item.

Of course, they are not substitutes for solid lending criteria, well-established practices, and the relationships that form the basis of most successful loans.Alternatively, investing in a syndicated mortgage fund will defer all loan management to a sponsor, who would take care of this for you.

To some degree, you can substitute one for another.

They can walk you through all of this and will help you create a tax strategy based on your goals.Your statement that "insurance can't be deducted" reinforces that it's most likely in your best interest to hire a professional to help you with this.The forums are great but not a substitute for hiring a tax pro.