A few things to consider: are you increasing rent each year to at least try to recoup some of the additional costs (everything goes up, so why should the family member not pay more-if it is your parents, it is more complicated), how much has the condo appreciated over the last 3 years since you bought it, and what would you do with the money when you sold?

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

Thirty years ago, it cost me $600 in labor and parts to replace a 50-gallon hot water tank, currently $1,500 and often they only last 6 to 8 years. 

Selling costs time and money. 

You could promise a certain amount of closing costs then take a few grand off at closing.

Looking at the entire nation for the top markets is great, but do you have the bandwidth to set up teams in those areas?

If it was useable before (small ding) and is now destroyed, I'd take her up on her offer, but I'd also pay some of the costs as it wasn't new when she moved in. 

Find othere cost saving iteams  on maintenance and capital improvements like LVT in the bedrooms ect. 

QBO isn't setup for rental properties or multiple rentals and when you have multiple LLC you need a subscription per LLC.

He's segregating costs on the buy, leaving me as seller with a 33% portion POC.