Sometimes it's ambiguous, but even then, why should I bother with the company that has numerous unresolved lawsuits, versus another company that is virtually the same but has none.

Additionally I would add a benefit for you is that you're in great area to be able to invest locally and can invest in your own back yard as they say.

My core investing philosophy is pretty simple, and has done very well across almost two decades and numerous cities:1) Invest in cities with population (and job) growth2) Invest in parts of the city where household income is near the median (or slightly below)3) Invest in properties that provide cash flow from day 1 Thank you for sharing that. 

Many lenders allow for low-down-payment options if the rental income covers the loan.You’re approaching this deal thoughtfully, but be sure to communicate the benefits of your offers clearly to overcome resistance from the seller's representative.

I prioritize appreciation, tax benefits (rental property expenses, depreciation), ability to use leverage, and passing on generational wealth with real estate. 

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

So there could be benefits from starting a new lease for that reason.

What are the limitations and benefits?

Of course to maximize your tax benefit it needs to be sustainable over time. 

As I wrote in another reply too - one more benefit for me is that in a way it's "forced savings" - I have to find a way to pay the bill...