Also, you should treat the duplex as your own home, so of course you'd get a policy to cover it!

Goggle this: "IRS real estate option treated as installment sale".

Speaking of which, if anyone knows, I'll find out soon enough, can you hand the post office clerk a stack on stamps and your attack of letters and they'll treat your stamp stack like currency, make the trade then stick your stamps in a drawer and then like 'rubber' stamp the letters for you?

Treat it as a business.

@Sue Matt In Maryland, Section 8 tenants are treated just as a "normal" tenant.

Treating it as a business seems so much easier. #2 Would the IRS rather I did that ?

Up till now I have been treating my, dare I say income, as capital gains. 

@Brian Campbell, I recommend treating each property as if it was the only one; do your analysis accordingly.

@Courtney Jones sorry miss read your post did not see the "not" primary, defiantly put in an LLC, you can easily do  a single member LLC yourself and you can actually treat a single member LLC as a "direguarded entity" for federal tax purposes meaning you can file it on your schedule e on your personal return.  

Basically the period you were paid under the table would be treated as a period of unemployment.