Paula: absolutely agree with you. As with any major decision, the crucial question is "what is your goal?" Of course, having resources to own something on 30-a is an important step. After that, though, the question (as discussed in opportunity costs, ROI, ROE discussions above) becomes "what else would you do with those resources?" We have been so very happy with our decision to buy a home in sowal. One that I hadn't thought about before the purchase was the fact that with a 2nd home, came more pressure to actually use it and take some time away from work and bring the family to sowal. We used to take 1 or 2 weeks off a year, now significantly more, and in the end, will probably extend our working lives by years. Forming lasting relationships with others who have invested in a 2nd home also has generated some tangible financial (and more importantly non-financial) benfits as well. Having stayed in rental properties here for 30 or so summer weeks prior to decision to buy, the numerous "hidden" benefits of ownership clearly more than make up for "cash flow" of the property.
Definitely, the "what is your goal" question is critical, along with "can you afford to buy it and still sleep at night in good and bad times" and "am I diversified?". In the years that I bought the cottages, I've seen them go from fantastic investments, to not-that-great investments, to good investments (given the stock market tanking). Also, one of my goals was "forced savings" - If I didn't have the SoWal mortgages, I know I would have been tempted to spend more money on things that wouldn't have brought me (and future generations) as much happiness as vacations in my own home in SoWal. For example, cars don't excite me at all, so I drive old cars (one is proudly going on 10 years old and I'm getting it tuned up for the next hundred thousand miles). I'm not doing a big upgrade in the old kitchen in my primary home though it really needs a lot of work - I'm just making inexpensive surface changes - maybe even a formica counter top and linoleum floor. Having the extra mortgage and wanting to keep the SoWal places makes me think carefully before I spend on anything - It's all about trade-offs and understanding what brings you lasting joy. I have several friends who paid quite a bit to completely redo their kitchens and they're very happy with that choice (and their kitchens are indeed beautiful and well-designed). For the same amount of money, I'm paying for 1/4 of a place to call my own in SoWal. It's about knowing your goals (as you said), making mindful choices, figuring out the trade-offs, and thinking about what will make you happy in the short and long-term. Not surprisingly (and thankfully), everyone has different answers to these questions.
But we like relative quiet and nice architecture and high elevations in addition to the gorgeous sand and water. When we bought, it was just our way of reserving our place at the beach.