1. I'm not very good at software installation and configuration. If it's anything more complicated then clicking on an EXE and possibly modifying a few visually driven prompts, I tend to get stuck and burn a lot of time getting nowhere. I know people who are good at taking packages and following involved installation and customization instructions but I'm not one of those people. Am I realistically going to need to hire a Moodle expert to get the software up-and-working with the look-and-feel that I want?Moodle installation is easier than most web-based platforms. That being said, there are a number of critical issues in a Moodle installation that would best be handled by someone at least familiar with web and database servers. These issues are primarily security related and you can search on the installation forums for more information on how to do that.
http://moodle.org/mod/forum/view.php?f=15
As far as a look and feel, it depends on how far away from the standard layout you wish to go. Moodle has quite a bit of flexibility in the layout of pages already out-of-the-box. Working with colors and fonts will require some knowledge of CSS.
2. What sort of effort/timeframe should I be expecting to do the sort of customization that I described above? Not having worked with the product, I don't know if I should expect it to take a week or a few months.It all depends on how much work is needed and the avability of the developer. However, I would not think that it would take a matter of months to do.
We're at the Custom Build vs. Use Moodle decision point in the project but Moodle is such a black box to me right now that I find it extremely difficult to guesstimate what costs or effort would be involved with adopting Moodle.Your best bet is to contact a Moodle Partner in your area (Canada?) for a quote. At least you will have an tangible figure on which to base your decision.