Why not deal with the uncomfortable moments and turn it into a satisfying one.         

She seemed shocked that you were hesitant in moving forward with a simple assignment contract…I agreed.She said she could walk you through how to handle an assignment if you felt nervous or uncomfortable.

Beyond the mortgage, my expenses include taxes ($6K per year), insurance ($1200 per year), and obviously any capital expenditures or routine maintenance that comes up. 

So if it is the difference between doing this or being to uncomfortable to take on something bigger then it's probably worth it to do it condo or not.

The list is long and courts have routinely pierced the veils once a civil tort is proven.

I would definitely avoid routinely picking up the rent at all costs.

Even though the money all ends up down in your AGI on your taxes, some underwriters get very uncomfortable when they see small salary and large K-1.

At the very end, after they had already gone through final conditions and we were just waiting on the clear to close, they backed out.Some manager somewhere along the way said they were uncomfortable because the private lender was a relative.

Reminder her that relationships with neighbors can be tricky but they are best handled between the people involved even though it is uncomfortable.

@John Teachout I totally agree that they are personal questions and some may find it uncomfortable to answer.