Waiting 6 months no only gets you the full exclusion saving you possibly as much as $63K or $125K (25% of the maximum exemption of $250K in gain or $500Kin gain) in taxes but it also gives you 6 months more of appreciation and has you selling the house in the prime spring selling season.  6 months reaps a mighty potential reward.

We are about to purchase our first rental property and are a little nervous about finding renters during the holiday season.

Not seasoned by any means but have done about 12 or 13 deals. 

Seasonality: Chicago Airbnb, like Chicago real estate, is seasonal.

I am a seasoned single family investor that has an interest in parks, and put my first one under contract.

This gave me the ability to contribute up to $5,500 pre-tax at my own discretion to limit my tax liability come tax season. 

Between dividends on stock in my family's ranch, rent from my girlfriend, tax returns, overtime worked during my busy season, I have around $20k a year extra after my mortgage and living expenses that I put away.

I am a seasoned IT professional (UI/UX & Multimedia Design).

Method 4: Negotiate a 60-day owner finance.If you find a seller willing to give you a very short-term owner finance (you may want to go 3-4 months just to be sure), you can get the deed in your name and refinance it with either a local bank that doesn't require title seasoning (The same bank that gives me a 15% down payment requirement will also refinance the house based on current value (not my purchase price) as long as the title has been in my name for at least 30 days).If you can't find a bank that will do that, I can do it for you.

The other straight-line hairlines on both the ceiling and walls are likely the drywall seams that have flexed a bit due to the house settling, and seasonal shrinking and expanding from temperature changes.