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. 

(We have fixed up 3 houses now and primaries not fix and flips and really enjoyed it) my job also works 1/2 the year so I have plenty of free time for rehabs.Option 2, just purchasing a long term rental with the cash out but this will produce a negative cash flow due to the cost to rent in the springs area and $0 down.

Selling costs time and money. 

There are some good people in business, but there are also nasty, hateful people that will cut your throat for few bucks.

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

Househacking is all about cutting down on your living expenses, and that means different things to different people.

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. 

It could just be a simple consultation that doesn't cost much.2.