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Cheap Hotels

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Catch the trend, here?

I scored all of these amazing deals by doing one thing, and one thing only.

I traveled off season.

Traveling off season or during the low season, simply put, is the time of year when a destination gets the fewest visitors. As a result, amazing hotels are plentiful as they tend to offer the lowest prices to attract customers and fill rooms. Scheduling some of my travel during this season has been the easiest way for me to secure the best resorts, vacation packages and flight deals. People always say that the weather off-season in most places is horrendous (hot, cold or rainy), but often, it's quite the contrary. If you're ok with a day or so of possible shoddy weather, traveling when there aren't many other tourists around is an attractive option for many. During my stay at each of these locations, the weather didn't hint at anything out of the ordinary (with the exception of Bali). In fact, I couldn't have asked for better weather.

My Friends and I Bought a Condo in Hawaii

On Tynan

My friends and I have individual condos in Vegas, an island in eastern Canada, and a flat in Budapest. It's not the same group for each property, but there's a lot of overlap. I realized that none of our places are ideal for winter, though Budapest does have its charm, so I started thinking about tropical places that would be good for quick escapes from winter (it even gets cold in Vegas).

When buying these shared places, cost is a major factor. The property has to be cheap enough that everyone can afford it without needing to go there constantly to make it worth it, and also so that no one ever needs to sell to free up cash. Every property we've ever bought has been under $100,000. Those factors eliminated a lot of popular winter spots.

My first choice was San Juan, Puerto Rico. I had been once and thought that it was a really cool city with a mix of good beaches, good healthy food, and a nice downtown area. I sent out an email to my usual group of friends, got a group together, and booked a cruise that ended in San Juan so that I could go check it out.

In the meantime the hurricane hit, but I was undeterred. I figured that I could see which buildings could survive a hurricane and if I still liked the city at its worst, it would only get better from there. Plus, maybe some people would want to move to a non-hurricane-prone city and prices would be good.

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