I try to put myself in his shoes and just feel terrible about the situation.

We’ve all been in your shoes at one time or another, unfortunately.

If I was in your shoe's I'd go with the multifamily.

Even if I raise it from $600 to just under $1200 in the span of a month the tenants have no where to go because I will still have the cheapest rent in a 5 mile radius.Though, I don't want to be too harsh as I have been in their shoes before, I will work with them on the rent raises.  

Most in your shoes believe the time to raise capital is when their own money runs out.

Buy a cheap pair of decent basketball shoes and a ball. 

My agent refused to take her shoes off because of the smell.

There's a lot of investors who are in Arron's shoes and don't share the struggles  they face while selling their lower tier inventory.

I am replacing the balances and pivot shoe locks. 

@Kevin V. if I were in your shoes I would fix up the Carlsbad house and keep it as a short term rental that would still give you the freedom to use the property and keep it in the family while maximizing the rents you could get.