@Todd KalseyI think the biggest key is just continuing to watch your market and time your improvements accordingly.

The Biggest Risk Factor is Overnight Risk or in counting on long term Appreciation with real estate.

the biggest issues are that the available tenant base drops dramatically around October and doesn't pick up again till the end of the school year.People are no different than animals in that regard.They want to be settled and hunkered down in a property before the school year and/or bad weather starts.Quality tenants with good financial backgrounds don't want to move their families in the middle of an icy,snowy winter for obvious reasons,and good college students have already started school in August.Many of the few available tenants will have questionable backgrounds like recent job loss,previous eviction,bad credit,difficult income verification and don't make 3 times the rent,criminal records,etc.   

The biggest thing I can bring up is this...

Handwrite the signs with the biggest Sharpie you can find, something like:WE BUY HOUSES!!

My biggest concern is not with the renting in December.

@Dave BolducAs a landlord, asbestos, lead paint and mold are probably the 3 biggest liability issues.

Financing is going to be my biggest challenge/most rewarding hurdle at the moment.

Obviously my biggest fear is a bad tenant.

Not only does it give you downside risk management (lots of podcast guests, as well as Bloomberg and other news sources have been talking about weakness or coming weakness in RE markets), it also saves you money by giving you more cash which you can use to pay the loan off early.