Dear PoP – How Much of a Pain is it to rent out a Condo?

Photo from PoPville flickr user Sanjay Suchak

“Dear PoP,

I’m thinking of possibly renting out my studio condo in a couple years and possibly moving out to the Arlington or some other area where I can rent a bigger place for myself. I still have a mortgate on my condo. To be honest, the prospect of renting it out and all the potential IRS hassle that comes with it (depreciating the property, deducting condo dues, etc.) scares me a bit, possibly enough to avoid the whole process, especially since I’ve always done my own taxes. Is it less scary than it seems? Is a tax attorney necessary to handle this scenario or would TurboTax or similar software suffice? I envision my overall federal/DC income taxes going up if I make this move since mortgage interest/tax deductions would now be used to counteract rental income.”

For those who rent out your condo and/or house – how difficult is it re: taxes and in general? In your experiences would you recommend it or if it is feasible would suggest trying to sell first?