Meet ups are great and maybe with a mindset shift I could benefit more from them.

What's the benefit of the $149 sub through TurboTenant?

Real estate is a long-term play and cash flow is the last benefit you receive.

Plus we'll still benefit from appreciation, loan paydown, equity, etc.

Rentals generate passive income, so an S-Corp offers no added tax benefit.

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. 

Chiefly Im looking at it from a tax benefit stand point, but also want to make sure the principal investment is secure as possible.

Mis-represenation of tax benefits.

Imagine the $hit posts that would result.I question the benefit of getting points for using the calculator.I think the points should reward quality and not quantity. 

But cashflow can be just as important to a small business (and your mental health).