My parents were contemplating buying my grandmothers house after she passed and selling their home, which just so happened to be around the same time we started looking at houses.

So if you contemplate to sell vs refi, consider the tax advanatage (and don't sell). 

Stuff happens.However, I think the *real* issue is that my agent miscommunicated to me on TWO occasions about the repairs.First was this, when I was contemplating the purchase (emphasis mine):"Also, regarding the disclosed repairs for the other building.

I had contemplated cashing out the entire IRA to invest until I heard about the checkbook IRA(and tax consequences/penalties).

I am contemplating being a podcast guest on this subject, but here's the gist of my 'leaving a legacy' story. 

I've had one tenant I was contemplating using a service like these on, but I was ultimately able to collect all of the money owed to me through the court/wage garnishment process.

I have contemplated the idea that maybe there was a leak and that's why the bills were so high. 

I own two homes, one of which is my primary residence, and the other being an investment property, currently being occupied by my parents. They have been paying us a minimal amount of rent over the past 2 years, while...

@Dimitri PaspalarisHi Dimitri - I've been contemplating doing the same. 

However, I still would like to contemplate my other options.