Since then I have only owned my primary residence and had not invested in rental properties. 

The budget for closing presents can differ, depending on the broker's budget, client tastes, local practices, branding, and timing of presentation.

A second home would be financed somewhat differently than a rental property.Advice:  speak with a broker, an attorney, and a title company. 

We have also had, historically, a 5%-ish difference in rent rates when renting out in December and January as opposed to other months.

Everyone is a little different.

Single income (married with kids) and own primary house with $250k+ in equity. 

Tax free gains-  primary 2/5 years up to $250k per spouse versus 2% tax free munis.  3.  

David,Since you have no mortgage have you thought about doing a cash out refinance on your primary home. 

There are so many different ways to structure each deal. 

And, if I (an appraiser) decide I need to use comps in a different area, I should analyze the area and see if any location adjustments are necessary (i.e. are those comps in a more desirable area/location, etc,).