For me it depends on what is the lifetime value for a customer. Very easy to determine if its a one time fee. And what is the lifetime expense of a customer. If the expenses (server cost, support, etc.) grow over time, then you are bound to lose money. If your application is one would only be used a few times, say wedding planning, or related to being pregnant, then I can see it.
The big downside I see, is how do you handle upgrades. With a SaaS subscription model, they are continuously paying for the upgrades. With a web app with a one time fee, you would either have to give them the upgrade for free, force them to pay for the upgrade or maintain multiple versions. With desktop apps, it seems that you get a big boost in sales with an upgrade and I feel like you miss that with a one time fee for a web app.
Remember that most desktop software run as standalone programs, so there isn't an ongoing expense of servers and bandwidth. It is also much easier to charge these users for upgrades later on (at a discount, usually).
With web apps there is an expectation that the product will continually be upgraded even when they're free (think Gmail or Google Docs), so it's harder to justify charging for upgrades.
You also have to consider that some users might only use the app for a few months, and others for a few years. Should I pay the same if I just need your app for a short time?
Most web apps, like project management software, fit nicely into recurring monthly/yearly payments. Unless yours is very different from that then it's probably better to do recurring. You'll have recurring expenses to pay to keep the site running, so you'll need recurring revenue to cover those.
I don't actively push new updates. This month I set aside a few days to rework the interface a bit but other than that the feature base has been pretty static since launch.
I would guess that it would only make sense for software so cheap that recurring billing didn't make sense. ($10-20 total lifetime value of a customer).
The trouble is that getting customers that cheaply is difficult, and even harder to scale. Upselling existing customers with recurring revenue can be much easier than getting new customers.