I think it was Adobe that forgot it was a company that makes tools. They did make it Flash versus HTML5, and are now realizing that they should have been agnostic as a toolmaker.
I tend to think no. For a small site with few users, no one will care. Once a site has become large enough, downtime with press coverage seems to create a virtuous cycle of social proof, e.g. Twitter, Facebook, etc.
Most of these have the best support for PHP which may or may not work for your needs. Various free libraries have been released for other languages but 1) generally support only a few email providers and 2) may not be actively maintained. Octazen has a fee-based API which sounds great but I haven't used it.
I think the subtle point here is that users don't want bloated applications but
1) They will vocally advocate for additional features that meet their specific needs
2) They will buy upgrades (particularly of boxed software) based primarily on new/additional features
I think this article has some good tactics. Three additional points I would add:
1. An incredibly valuable skill is being able to clear your mind and see what you're working on from the fresh perspective of a potential user. This is even easier if you are your own target audience, or if your product is such that your team can 'eat your own dogfood.'
2. Don't forget that usability testing typically only makes sense if the participant is in your target audience. If you are targeting some sort of specific niche audience or need (and most businesses probably are), it's worth taking time/$ to find the right kind of person versus someone online who has no context for the need you're trying to solve. If you already have customers, some of them will almost certainly be excited to help test new features.
3. If you're doing research interactively, consider having someone who didn't design the product asking the questions: it's really easy to bias the results based on your expectations.
Finally, it's certainly not cheap but if you ever have a chance to do usability research in a lab with genuine 1-way glass, it's a blast!
First impressions: I really like the overall look & feel of the site: approachable, modern, clean, and not needlessly "web 2.0"
I have trouble knowing from your messaging who your target audience is, and whether I'm in it. E.g. needs for someone who travels casually and who is accruing miles towards a particular vacation would be very different for someone who travels for a living and has dozens of accounts to keep track of.
For me, I've mostly standardized on United Mileage Plus and therefore make sure that any reward programs I participate in are compatible with United's program. Therefore, United's site serves as the aggregator for all my mileage/reward programs.
As others have mentioned, the key distinction is whether you're targeting individuals or businesses.
Typically you'll have a tough time convincing individuals to part with $20 per month and typically there's a free alternative.
It's much easier to convince businesses to spend the same amount and, as a bonus, many will be suspicious of free offerings. In fact, others will subscript to a higher premium tier purely to "buy the best for my business."
As a customer, I hate getting gouged by text messaging.
As an entrepreneur, it gives me hope that there are useful services which people are willing to pay for directly. The social/viral distribution of sms is impressive: it costs me to send a message to my friends, and I'm encouraging them to spend money with their provider in order to respond.
The reason I left a cushy, high-paying job was that I think I can always get another cushy, high-paying job even when I'm older. On the other hand, my mid-twenties are years when I can afford to take (calculated) risks and do all the things I know I will have regretted not doing when I'm in my 30s and 40s and have more responsibilities.
I was also surprised how many people at and above my level in a big company seemed envious that I'd go to a startup.
I agree with you that the writing is often not great.
On the other hand, I see a disproportionate number of "Top X reasons"-like posts hitting digg and delicious/popular which leads me to believe that lists resonate well with readers. I'm not a blogger or link-baiter, but I'd prefer to write a mediocre article which is read thousands of times via prominence on social media sites versus a 'well-written' article with no numbers/lists that no one reads.
It seems like consumers of blogs and social media like lists, so bloggers logically satisfy that need.