My fear in regards to this is it would be extremely hard to say rent out as a long term rental and still maintain any kind of cash flow if the vacation rental side is not as strong as you think.  

I analyzed around 100 properties before I finally pulled the trigger and got over the fear thing.

IE its a high crime area and you fear for your safety.

I'm going to use wisdom, and not let fear rule.

@Matt HoneyfordIt's hard to take the fear out of someone's heart if that person is naturally risk-averse.

You will need enough allies to take over the board in the next election or the one after that, depending on how many seats are open each time.Just as people with bad dogs think it's no big deal to have their dogs destroying property, barking and creating fear in neighbors, many people who own commercial vehicles, trailers, unused portable basketball hoops and junk cars have no appreciation that other people don't like their stuff and don't want to look at it.

I'm not one for timing the markets, but the best time to buy is when others are fearful and running!

I was raised to have a very frugal mindset, so even to have the option to buy something without having fear of not having enough money down the road is freeing in itself.

The hardest part was just getting the fear out of the way, after that it was simply a question of staying on top of every situation.

In addition there is street parking all around and many other residential apartments buildings and commercial buildings (Wall Mart etc.) that help make it a very walkable location and may accommodate occasional overflow.To me 2-3 dedicated spots seems like very inadequate parking for many potential commercial tenants and I fear that would make owning this investment a challenge.