My biggest issue is that many people don't fully appreciate the time it takes for a professional web design and development project and that they should actually pay for it.

One of the biggest problems I've run into as a freelancer is building trust in new clients who had a bad experience with a previous web designer / developer.

A big pain for me is quoting. I expect to not hear back from a large portion of the people I quote for, as I don't pitch myself cheaply, however the time it can take to prepare quotes covering detailed requirements can eat away at actual "work time".
Another one ... when I started out I did several "mates rates" jobs for people who wanted lower cost work, these have now turned into the thorns of my beautiful bush. Still wanting little or no cost but demanding bigger and better. I now know to do a good job AND charge for it.

I started using Cashboard for quoting and it saves me tonnes of time. It even lets me import items from past estimates so no repeat entries and less chance of missing stuff.

I concur! A similar (not too bad) problem for me as well. I did get around this by developing a 'template' of items that are almost always covered in price-quotes and then simply add or adjust items per individual client.

My problem is actually finding the work and holding on to it. Especially after I talk about pricing, even after I offer discounts.

Don't offer discounts? At least I don't I will at the end of a project add some value to the work. My last client I sent the invoice and mentioned that I installed google analytics even though it was not in the site plans. Told them why it was a good idea and it was provided free of charge.

We know that didn't take me long at all but gives the customer extra value. I also found that when I raised my rates I got more work. Seems weird and tough when your lower rates make people walk away but that's what happened.

Great stuff so far, folks! Keep it coming.

One of the bigger challenges freelancers face, in my opinion, is with the business side of things. One can be an amazing developer or designer, but if you don't have the people skills to work with clients or the ability to actively drive sales (or can find others to do this for you), you're in trouble.

I agree with you 100% -- I spend a great deal of time taking care of the "business" side of things when all I really want to do is the creative aspects of being a designer. In order to be successful as a freelancer, it does become necessary to develop people and business management skills.

I'm fairly new to the freelancing world and would consider myself a part-timer as of right now. I think, as a newbie, the biggest issue I have is self-motivation and scheduling. In the past few months I've had to find out where my most 'productive' environment is, and to be honest, I don't think I've found it yet. I'm trying to change up my routines.

Scheduling myself is another beast. I'm new to the setting my own deadlines concept and again, I'm still working out the kinks in that department.

It was recently suggested by a close family member to read "Getting Things Done" by David Allen. A fairly inexpensive 'tool', which could prove valuable. Has anyone read this book and found it useful?

My biggest issue right now is sales - I am a terrible salesperson, even though I know my 'product' is good and my price reasonable. The thought of cold-calling or walking into a business and pitching my skills just makes me sweat, and keeps me from landing some decent projects. I just don't have the skills to that side of the business on my own. Bookkeeping, project management, creative - I can handle all that, all the behind-the-scenes stuff. It's just the apprehension of a face-to-face approach with potential clients that's holding me back right now. People keep telling me to just get out there and do it, that the more people/businesses I approach, the higher my chances of landing projects will be. My fear is that I'll get out there and approach endless amounts of potentials, but do such a bad job at pitching that my reputation gets damaged. I had an unofficial partner that was really good at pitching, and when we both approached potential clients it always worked out really well, but that partnership has faded away due to the lack of availability of the partner. So now I'm stuck going solo, and having a tough time at it. So what I need right now is a sales person, or an agent, or a kick-ass marketing campaign that drives people to me, instead of me having to drive to them.

My issues have been mostly with collecting payments and being taken advantage of. I have no real way of dealing with the "I'm waiting for someone to pay me so that I can pay you" or the "we hit hard times" lines. How do you respond to that when you know so many others are having a rough time financially in this economy? I find I am giving away work because I understand how hard it is for everyone right now, and I can't afford to do that either. I want to help, but I need to pay my bills and, I can't aford to hire a collection agency to do my dirty work for me - so now what?

You could offer a discount for payment now that goes away? I have thought of offering a discount to clients if they pay in 10 days of receiving the invoice.

One of the biggest things I have struggled with is finding a workable flow for projects from estimate -> working -> invoice. Trying to keep track of what was sent to whom and if deposits have come in can be a pain.