@Brian Foster great insight!

Many investors can stomach (emotionally and financially) "less money" or "break even" but can't handle negative cash-flow even if they're making up for it through building equity.  

I think part of that may be her emotional attachment (we know it's not good) because we are renting a house that she bought before we were married.

This is an emotional inquiry, not a business decision.You don't buy equipment based on what you think may happen.

Recommend you search up @Dave Foster's name and "1031 into a Syndication" and "Tenants in Common."

@Dave Foster Is the 1031 Exchange master!

That changes it from an emotional decision to a logical one (yes I am an engineer). 

I do believe that since its owner occupied there is some emotions in play.

Hi Benjamin,If it were mine, Id have this tree removed and the stump ground down to zero.A tree that sheds like this is not the type of rental experience I want to offer.Limbs are very heavy, and add to that the ice weight, and a renters best friend getting into a car with a baby and they are both crushed by a known limb dropping tree is a lawsuit (and emotional mess) I'd rather not have.Winter tree removal might be cheaper due to low demand and the ability to sell the firewood easier.Maybe a contractor in your area has one of these and can solve the problem in 30 seconds:  https://www.youtube.com/watch?

Keep emotions out of it.