Shelly:
I liked the article because it reminds the potential buyer of a second home to think about all the costs, as well as gains, involved in their particular situation. Though one can't predict all costs -- or all gains and other benefits -- it makes sense, of course, to figure out the costs involved in different scenarios. The article made specific assumptions (how much the house would increase in value, a 5 year time frame, etc.). You'd want to play around with different assumptions based on your personal needs. For example, how long a time frame? As for increases in the home's value, that's a tougher one, though I'm still optimistic about SoWal (if you don't plan on buying and flipping) and I think it will be much nicer than many other places that have gone "upscale" that have are primarily concrete and buildings with no green.
The other thing to consider is what you would do with your money if it wasn't tied up in a house. Frankly, a lot of people (e.g., two career couples) waste their money on things that don't increase in value (e.g., cars, too much expensive coffee even when blind taste testers consider some lower-cost coffees to be better, expensive lunches, etc.). One of the reasons that I wanted to get our property in SoWal, aside from how much we'd enjoy it and it's much warmer than Michigan in the winter, is that it would force us to be more disciplined about saving and managing our income. And that has worked very well -- and we don't miss anything we used to waste money on, though the kids are starting to get a bit embarrassed about our aging van.
As for renting to guests, we've been very happy. The rentals don't cover all the costs for sure (and one should never count on rentals to pay the bills), but I finished our taxes recently and the rentals covered about 2/3 of all our expenses. Not bad at all as far as I'm concerned. That's after 3-4 year of owning the property and the major expenses of furnishing the cottages are over, though taxes, insurance, etc. will continue to go up (but so has the value of the cottages). Of course, I put a lot of work into marketing, keeping our guests happy, working together with the management company, and maintaining the cottages -- but I enjoy that kind of work and I've certainly learned a lot in the past few years. One reason to do all this work, by the way, is that it does seem that there will be a LOT of rentals available and renters will have more choices than before -- so quality and service (and repeat renters) will become increasingly important if you want people to choose your rental over another.
I hope this information adds to the perspective given in the article. Again, I think the best part of the article is that it encourages people to consider all the costs, as well as benefits, of owning a second home. What the article doesn't cover is (once you can cover the costs) whether the second home will bring you joy, happiness, memories, peace, new friends and a community to belong to, a porch to read on that you can call your own, a warm uncrowded place to go in the winter months for walks on the beach and sunsets (the author of the article calls these "extravagences" though he admits that he has a "glass-is-half-empty" outlook on second homes, so it would be easy to miss these benefits with that perspective).