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A few tips from a smaller operator than Ron. I only have about 4.5 million Wyndham points plus about fifteen fixed or floating weeks outside the Wyndham system (about half of those in New Orleans, a place I know what it means to miss).
1. Running a rental business takes time!! Ron is in the real estate business so this is just another line for him. I manage military sales to a country in South Asia in a secure government agency. Of necessity, I conduct almost all my rental business at home in the evening and on weekends, the exception being some emails or calls on my mobile phone when I step outside the agency. Making reservations, managing rental listings, returning emails and calls, keeping the books is an enormous investment of time.
2. Specialize. Ron works New Orleans and does well there. I concentrate on two resorts where I own and have stayed several times -- Bonnet Creek and Ocean Walk -- but will book a reservation on spec most anyplace I've stayed and liked and that might sell well. I won't book a reservation at a resort I know nothing about unless someone asks for it.
3. Look for event/holiday weeks. New Orleans is a festival town. Daytona has Bike Weeks and races (I work Bike Week but not Race Week). Bonnet Creek is a very high demand resort for vacation periods -- spring break (secondary schools -- avoid college spring break), holiday weeks. Mid summer at Skyline Tower in Atlantic City has been popular but may not stay that way.
4. Don't get greedy. It's better to rent a week at a lower margin or even a slight loss than it is to have to keep cancelling unrented weeks and booking later in the year and maybe eventually lose points. Watch your use year.
5. Learn how your listing sites work. TUG is good because you if you sell a week and the listing has some time left, you can change it to another resort. RedWeek.com will let you change everything except the resort.
6. Don't mess with the IRS. You can probably get away with some accounting mistakes on the expense side. But, always report income.