I was looking into buying a condo in the Island West development in Davenport. HOA is reasonable at ~$200, there is a small pool and gym, etc., but I just learned that I have to pay a "HOA Initiation fee" of $5k. This seems very odd to me as I thought those were only charges when the units were first purchased. As a northerner who doesn't live in the area I am wary of being sold a raw deal.

I own a couple of investment condos in 3 different developments in the Orlando area and I've never had to pay an initiation fee. That seems very odd to me too, despite $200 being a reasonable fee in general... 

I bought and sold a property in there like 2 years ago with a client.. It's a cash grab from an HOA that is financially unstable. It's a nice community with decent amenities but that $5k fee is unavoidable for those couple of complexes in the area. Most sellers list their units accordingly because they know the $5k is a big issue for buyers. Are you looking for a vacation rental in that area?

Hi Jared Maltbie, yes I am looking for a vacation rental the I can Airbnb part time and use part time.  I like that there is what  I would call a mother in law or accessory dwelling unit with a normal tenant that will help offset the mortgage.  

Some resort communities have an HOA initiation fee which from the sounds of it that is where it is. I'd definitely skip it because that is complete BS fee that you'll never see again.