@Ray SlackAlso see IRS Publication 560 as it contains good information and calculation sheets. 

Hop on airbnb, put in your area with no dates, then hit search.

The TIC structure was selected due to the other owner bringing in 1031 monies and to not violate IRS rules regarding identical SS#s for the sold-new property.

My suggestion to most of my clients for this is an LLC that has elected to be taxed as an S-Corp with the IRS (aka S-elected LLC). 

In terms of tax help get an experienced CPA that knows RE tax specifically.If you're truly interested in learning the tax game I would recommend you do the following-Read through IRS publications pertaining to RE tax.

Business profits will pass through the S Corp to its owner(s) but the IRS typically requires that some portion of the businesses proceeds pass to the company's owners as salary or wages instead of business profits.

After 2 years, the IRS doesn't want to hear about your capital gains (up to $250k for an individual).

If I had any damage, I would just hop on top, scrap off the shingles/felt myself and get it replace fairly cheap.  

If greater than 20% of the income in an S-Corp is generated from passive activities, then the IRS may revoke the S-Corp status and convert the entity to a C-Corp.  

I'm not sure if this structure will constitute "prohibited transactions" under IRS rules.