Remember, there are two types of condos in a vacation area. The first is an apartment or townhouse type of condo where the residents run the association and the units may or may not be rented out. These are residential condos.
The other is a vacation condo where the unit is expressly designed as a transient rental property. Think of this as a resort with a front desk, operated by a professional staff. These seem to be hard to make money on, as there is the revenue split from rental, taxes, and maintenance assessments. If the association decides to re-carpet the lobby and re-stucco the pool you will be assessed. And, there are specific time limits as to the refurbishing of your unit. When it is time to refurbish, you get assessed.
The other issue is the amount of time an owner may occupy his own unit. Since these units are often considered sub-standard housing due to size, the municipality may limit owner time. Also, the association, which is in business to rent units, will often limit owner time, or even charge a nightly fee (yes, you may pay to use your own unit).
Vacation condos are seriously cheap in Door County. The reason is that the owners did not make enough money to offset the costs, and they caused negative cash flow. Now they need the money and will sell way below cost.
Still, a value is a value. Understand the costs and occupancy restrictions and you may be able to make it work. Just be prepared to write a lot of checks.
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Also, remember, if you buy into a vacation condo you are investing in a hotel. Look at it as a hotel and pay attention to how it is being run, how it is being marketed. Get the rental income statements for 3-5 years. Check the rooms. Look for dirt in the corners, look at the pool and spa. Read the Trip Advisor and Yelp reviews. Don't buy into a run down place just because it is a deal because you will pay to fix it.
