Or is the risk of having them grouped together outweigh the LLC costs and tax preparation and checking issues?

In my opinion, the good outweighs the bad for sure. 

Running negative every month is stressful and hoping for appreciation to outweigh your cost of borrowing money is like playing the roulette wheel IMO.

If the only benefit of holding a mortgage was the interest deduction, there is no argument that the benefit doesn't outweigh the cost (just like you shouldn't get married or have kids just to the tax benefits).But, just like with marriage and kids, the benefits of mortgages extend well past the tax benefits.These days, with interest rates so low, any decent investor should be able to earn more than the rate at which he can borrow.

That's why I quit paying attention in estate planning class JScott...the benefits didn't seem to outweigh the risks for me.

If you feel there is enough hope to go on, then you can make a calculated risk if waiting for her payment outweighs an eviction/turnover.  

There are a lot of other pros and cons, but that's a huge plus and outweighs a lot of cons.

While I still make title mistakes on occasion the gains from use of what I've learned and apply far outweigh the mild errors.

With this, you do run the risk of it breaking down after-hours, but you may also have another year of life left, for which cost savings easily outweigh even an after-hours replacement cost.You are already ahead of the game by knowing it is old and looking into it!

Minimized risks doesn't mean as great a reward but several have figured out that a lot of small risks in the long run outweighs the one big risk.