After that I'd just go with either annual or monthly depending on if you know you'll need to use it for an entire year, because it does offer a discount by going annual.

The seller managed to purchase at a time where prices were still depressed and purchased through a short sale allowing a steep discount.

If you plan on buying additional homes with this person, I would just let her enjoy this easy sale because the next one might be much more difficult. 

In addition to above, the lack of core investment opportunities, and inadequate inventory for proper diversification are critical issues that the industry needs to solve.At the same time, I don't think all of them are going to end up in a ball of flames.

Also, taking strategic acquisition approach in purchasing especially in a  depressed market is like couponing at a huge sale and then adding a coupon on top of the bulk discounted price.  

I simply add something like the following to Block 20 ("Additional Terms"):"Buyer reserves the right to finance a portion of the purchase price, but is not requesting a financing contingency".Obviously, if your financing falls through in this scenario, you are obligated to cough up the cash to close, or lose your deposit.

During this time we can decide if we like the area, while searching for other areas (perhaps less touristy) and if so, purchase an additional home in a traditional residential area and use the "vacation" home as a rental?

The house cost $80K, the first renovation was $57K and enclosing the patio was an additional $12K. 

I'm sure there are plenty of people out there who have successfully used an online company so I wouldn't completely discount that idea, just for myself personally I'd like to sit down and figure out what's best for the type of investing I'd be doing..Best of Luck!!

In addition to managing properties I have a background in Marketing and can honestly tell you that lead generation isn't a magical fix-all term. it's a lot of hard work and often a big investment is needed to start seeing results.