I'd like to chime in and say to not forget about having a fall back fund for any unexpected repairs in the coming months after purchase and repairs are complete. 

Since I've owned for more than 2 years and lived in it for at least 2 years, where does capital gains tax fall under?

Similarly if a tree falls on the house destroying it, the contract is void.If escrow has closed, then the heirs inherit the proceeds from the sale not the right to sell it.Talk to an attorney.

The reason he is buying at a faster rate is due to an inheritance and he starts business school in the fall which will make is harder to purchase.

I'm actually looking at purchasing some land and building a smaller house for myself and renting out the whole place either in the fall or spring for the next academic year. 

Ask if they have any issues that you may be able to address.I treat tenants as customers and have empathy for them - give them some leverage when they fall on hard times - but be firm and let them know that this is your business and you depend on the rent to keep your operation running.There are times when you can supply the tenants with up-grades, Frig, new stove micro wave - with those items supplied you'll be able to increase their rent a little.Treat your tenants with respect - thy are your customers and their rent pays your mortgages and gives you an opportunity for a wonderful cash flow and future retirment.Cheers

You have to plan for when your interest deduction falls below the standard deduction on your income tax return.  

If you rent, then most of the costs of owning fall on the property management company.  

Hopefully someday from the perspective of an investor as well, I've been thinking Troy would be a great place to make some investments and I go there every fall for alumni weekend anywayAlso, I wouldn't have known to look for the FEMA flood zones when buying in Troy but I can tell you I was there when Irene came through and there were quite a few buildings underwater near the river.

I would fall on my sword with the City.