I think a lot of this depends on your expectations. I bought five years ago knowing that I wasn't going to retire for three or four years. I was lucky in that the previous owner left a lot of good, usable furniture so I took pictures and posted the home on villagershomes4rent.com; cost was around $140 per year. I managed everything myself, I found rental agreement and security deposit forms on the internet and used them for every renter. I set up an LLC (under $100) to keep income and expenses separate from my personal stuff. My home rented easily in the "high" season, and had excellent renters from January through April; these same people have become friends and we hang out together when we're all in TV at the same time. Renting for the 3 or 4 months during high season covered my annual mortgage costs, renting any other months was just gravy. I had no other experience being a landlord but found it much easier than I thought; I was able to manage everything from 1100 miles away; you'll be able to find any help or maintenance people online or word of mouth from neighbors. Again, this all goes back to your expectations, I wanted to have income and tax breaks while I was still working and used the rental income to pay for a new roof and HVAC system but I did not have expectations that this would produce a profit. I did not make a profit in any of those years but the carryover losses helped lower my income tax hit. I would do the same scenario in a heartbeat, it was fun and rewarding for me but you have to have a certain mentality to do it. If you or your wife are worriers and are going to stress out about minor things this is definitely not for you, if you're able to roll with stuff you'll enjoy it as much as I did.
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