Skylight - installing a new roof, thoughts on a skylight?

[Andrew Mestdagh]

Hi BP Nation!

I'm putting a new roof on a home that I'm planning on living in for 3-5 years, then holding on to it as a rental property and/or eventually selling it.  It's a 1200 square foot Bungalow in the northern suburbs of Detroit.  The tentative plan is to install a skylight in the upstairs bedroom of the Bungalow.  I have a couple questions (below).  Any input or feedback, positive or negative, is very much appreciated!

1)  My quotes for a new asphalt shingle roof range from $4,500 to $5,500.  Any idea how much extra a skylight would cost to install at the same time as the new roof?

2)  Do skylights or the framing need updating more often than a typical roof?  What are the maintenance costs?

3)  Are there any extraordinary challenges to install a skylight during the winter time in a northern climate?  (I would not DIY)

4)  Other than extra natural lighting, any other major benefits to a skylight?

5)  Any major negatives to a skylight?

Thank you BP Nation!

-Andrew