Renting your property at the Lake of the Ozarks provides several options and also a sense of finacial security for the future. I have rental condos myself, so I practice what I preach. I also manage the Lake's finest Vacation Rental company, Pinnacle Vacation Rentals.
I have found the key is to determine a "business plan" for your condo, with the starting point of how many weekends in the summer you will want to occupy the condo for yourself and your immediate family. This will determine if you are running a rental business, or simply renting out your vacation condo.
Even if you are not going to rent your condo out, it is nice to know you have this option as a source of income. I've had people that have transferred jobs out of the Midwest that rented their condo while they had me market it for sale. They were pleasantly surprised to find out it was lucrative enough that they took it off the market and kept it as an investment, to sell at a later date or after the peak rental season.
As far as the IRS is concerned, your rental condo is either a business or a vacation condo. The key number here is 14 days total. If you rent the condo for 14 days or less, you don't even have to claim that rent as income on your personal taxes. It doesn't sound like much, but imagine that you rented your condo for 4 nights on the 4th of July, 3 nights Memorial and Labor Day, and one other time when you are not using it for 4 nights. What if your rent was $250 per night, and you cleaned the unit yourself. You could pocket $3500 tax free! $3500 would likely pay most if not all of your annual assessments and a percentage of other operating expenses.
What if you want to rent your condo more than 14 nights, but also want to use it quite a bit as well? The rental season is mostly from Memorial Day to Labor Day, and you will pick up some early/later rentals outside of those dates. That gives you approximately 102 summer rental nights. Say you used the condo 30 nights yourself, and rented it 30 nights. You would be able to deduct your expenses related to the property at the percentage the condo was used for a rental, in this case 50% (your use 30 nights, total nights used 60).
If you are renting the condo, and your personal use is 14 nights or less, you have a business, and you can fully deduct all related expenses of the condo including assessments, travel to and from the condo. Furnishings, utilities, cleaning supplies, insurance, assessments, interest payments, payments for labor, all are deductible.
Here's an important tip: Nights you spend at the condo "working " on it, are not personal use nights. If you take a weekend to repaint, repair, supervise a remodel, or buy and replace furnishings, this does not count as a personal use night. Keep good records, a log wouldn't hurt, and have receipts ready to prove what your actions were.