I even purchased his cash flow board game to play with my family.

@Marko BukvaI'm not entirely clear on the plan and ownership, but there are potentially several different types of tax at play for a transaction like you're discussing - gift taxes, estate tax, income tax, property tax, documentary transfer tax, etc. 

I'm also finding that a single large repair can wipe out a whole year of income, making me wonder if cheaper cashflowing properties is the right play. 

Hopefully someone with tax accounting knowledge can jump in here with more detailed analysis, but I looked at this a bit several years ago...1) You still have to pay the depreciation recapture on the sale decreasing the net benefit of this approach due to the large tax payment in the 'sale' year2) The LLC would need to not be a passthrough entity so that it can be taxed separately from you, so you have to add another tax return cost for the years going ahead3) Taxing it separately from you likely means corporate status and corp. taxation rates which are higher than yours and I've heard many times over the years to avoid titling real property as a corp...Overall from what I've seen this only makes sense in a select few scenarios, which for most people aren't in play. 

You’ll either need to focus on high-cash-flow opportunities or equity-building plays (forced appreciation in value-add properties.

To play devil's advocate (and keep in mind I have no skin in this since I'm in a different market):-You want to tailor to investors, then be prepared to sell at an investor price. 

Selling means giving up an incredibly cheap cost of capital, especially in an appreciating area like 28277.I direct my investors to 28277 all the time for appreciation-focused plays.

I'm Jessica, born and raised in Rochester, NY, where I enjoyed playing soccer and lacrosse.

Do some digging to see if there is something more at play or if he is just being difficult because he is a difficult person.

You definitely need some WOW factor in play here!