1. You say it's an affordability calculator, but it seems like it's based mostly around getting an opinion from the community. I finally found a "View Expert's Response" button which seems to do the automated calculation. You should either continue to describe/market it as you do and make that automated calculation more visible/central to the site, or leave it as it is but describe the app differently, as a community response app. Right now it's mixed messages.
2. The design is ugly to me. The fonts are all over the place with various font faces and sized, there is no consistency. The colors clash somewhat and also lack consistency -- orange and red and 2 shades of green and orange don't go that well together. Maybe they CAN go together but with the rest of the site's design (kind of haphazard), they don't blend well.
3. You have some buttons that are orange and some that are normal form buttons, and some links that maybe should be buttons but aren't. Some buttons take you to a different page and some don't, some links activate a javascript expander and some take you to a different page.
4. On many pages there is no padding on some elements meaning no whitespace on the left and right side, so they abut against the edges and look clunky.
5. The Home / Login rollover buttons on the top nav bar aren't apparent as links, they just look like text until you mouse over them.
6. There appears to be no way to browse or search other people's questions, all you have is the recent questions on the homepage. I understand if you've only got a few questions in your db at this point but you should already have space to be filled, at least different ways of finding questions, by newest / most popular / searching etc
7. To answer people's questions you have to look at their raw financial numbers and draw your own conclusions. Most people can't even do this for themselves, that's why they live paycheck to paycheck because they have no idea how different numbers affect their affordability. Maybe provide some hints, based on how the affordability calc figures things, as to how certain numbers impact certain other numbers? Plus it's all on multiple tabs, you can't view the financial info all at once so you have to flip back and forth and try to figure out which numbers are important and how they affect each other.
8. The site is called Can I Afford It, but the domain is caniafforditnow.com. I know sometimes you have to make compromises because a domain you want isn't available, but this inconsistency makes it obvious to visitors that it's kind of a thrown together site and not a professional app, especially with the design of the site added in.
9. View details and X responses from the community on the homepage go to the same place. If you click on details, it should automatically take you to the question AND show the financial details of the person at the same time. If you click on responses it should go directly to the responses, including scrolling down the page to where the responses are (by using a # on the url)
10. Now that I think about it, the view/hide financial details seems unnecessary. Why not just show the financial details of the asker on the page all the time? It's not like you have a lot on the page, that would give you a reason to use the # on the view responses links on the homepage to scroll directly to the responses :)
11. You aren't really addressing why people would use your app. All you say on the site is "Get a second opinion before making your purchase." Well anybody can get a second opinion on a purchase just by asking whoever's standing next to them. Why use your site? Because of the community? Because of the automated affordability calc? Say that.
12. Your community is obviously lacking because it's a new site and you don't have a userbase. It's like showing a subscriber count on your blog when you have 3 followers. It immediately says to everyone that comes, "Hey I'm a nobody". Which is of course reinforced by the lack of consistency in the design, lack of consistency in the site name and domain, etc. Maybe either hide the numbers better until you get more users, by not showing how many responses for each question on the homepage, or simply make several fake accounts and have them answer many questions so each question has at least half a dozen answers minimum.
13. Why require people to log in/register to give their opinion? If you could answer yes or no (and comment why) anonymously, you'd get more responses for each question over time. Lots of tirekickers have opinions on things but will never register on your site just to do some bean counting / pencil pushing (accounting analysis basically) when they can barely do it for themselves, but they might at least give an opinion. People will register to ask a question, but most people won't register just to give an opinion unless they plan on sticking around to give many opinions over time. Of course you may have to moderate the responses more heavily if they can be anonymous to make sure people play nice.
14. Maybe you should explain better how your affordability calc does what it does. It's nice that it analyzes and gives an answer, but purchasing decisions are emotional. If somebody wants something but isn't sure if they should buy it, they've got emotion invested into it and aren't going to go to your site just to get a yes or no by some black-box algorithm that they don't understand. But if you say, made an article page that explained how it calculates everything, why certain factors are more important than other, what deal breakers there are, etc, and linked to that when the "expert opinion" is given, they might appreciate the advice more.
15. You should have the verdict of each question on the homepage as well as any browse/search questions pages, anywhere a question appears. It makes the user more involved if he can not only see the question but also immediately see "The community verdict is NO" or whatever, then he might be more inclined to investigate the ones he disagrees with, or even the ones he agrees with.
16. Little things -- you have no favicon. You have no meta tags. You have at least 5 external JS files loaded on the page, not even counting your jquery or analytics usage, plus 2 different style sheets. No big deal when you have no traffic like now, if you ever intend to have a lot of traffic you should combine these css / js files and only have 1 of each.
Basically, if I was writing your app from scratch, I would have every feature you have and then some, but would use half as many pages or less, half as much screenspace or less, smaller fonts, more consistent fonts/colors, and then would have room to add more and more features later, to get people really involved/viral (gamification) like badges for people who answer the most questions on the site, people who are most likely to give a "correct" answer (versus the automated calc or versus the rest of the community), more interaction like more space for followup comments on each question, etc etc.
This is a very simple app that could live on screenspace the size of a mobile phone, but you've obviously added it a piece at a time so it's gotten bigger and more inconsistent over time. Not necessarily a bad thing -- you're probably learning a ton! I've got plenty of projects myself that look this bad or worse (or did for a long time before I went back and fixed them).
Actually that would be my best advice -- take the site as it is now, list every functionality feature, every UI feature, etc, and make up a whole new design for the site that integrates everything you've done and learned so far, then release it all at once as a major redesign so everything integrates/fits better as a single whole instead of this haphazard melange you've got going on now.
(And don't take anything I said personally, I can be kinda harsh but if you're serious then this is probably the kind of feedback you want!)