Finding the right property regardless of your exit strategy is the job of a seasoned agent that is a fellow investor.

Thanks for the insight, I will surely pass this info along to him.Come on folks, its the slow season let hear more about Spirits!

Most likely a cash-out refinance won't be possible unless the loan amount is above 100k and the property is currently seasoned and rented.  

I am interested in purchasing a seasonal short term rental as a replacement ($500,000). 

I am a pretty seasoned investor from Canada who wants to get into syndication seriously.

We are very familiar with the area and have friends who live in the town, though we'd love to connect with anyone who has any experience or opinions on investing in this market... or experience doing furnished rentals in locations where there are peak seasons and offseasons.

Have you identified seasonality for your region? 

For all my seasoned flippers.

Vacation rentals can generate higher income during peak season, especially in a tourist-friendly are like Venice.

Yes, the spring/summer season sees demand ramp up, but that doesn't mean a house listed in December won't sell.If you buy in October/November, chances are you won't be listing until January, anyways.If I had a house completed on, say, December 15th, I would likely sit on it through the holiday season before taking it to market, but I would talk to realtors.