My advice is to save up and get the best windows that you can afford. $5500 sounds like a lot of money but going with a handyman installing windows may ultimately cost you more in time, aggravation and destoyed siding or interior walls that need replacing/fixing among other messes. Wait for a sale or, if you can stand it and live in a colder climate, have the job done in the winter or at least not spring and summer - you will probably get a better price. I have used handyman services (or at least faux-contractor) for my kitchen redo because of the cost and had to chase the guy down, oversee all the installations of the floor, cabinets and repairs, electical lighting, etc and still had errors that need correcting because he said he could do the entire job. Saving money in the long run by scrimping on quality is not the way to go. Don't take a chance on something as important as windows. Home Depot is great but not for everything. Now that being said, I'm in the process of installing a floor in my den myself because its a project that can be done by a non-professional. And to HD I go.

What you pay for windows is not how you should analyze what is the best investment. Purchasing a high quality, Energy Star Qualified window may cost you far less than the "cheaper" window. To understand whta factors are most important, including the impact your windows can have on the energy efficiency of your home go the Efficient Windows.org. Installation of the windows is a critical item in ensuring the investment you make and can have disastrous consequences if done wrong. Here is a link that gives you a basic view of the AAMA approved installation. You will not find the top line windows at the big box retailers, you will find the lower lines and more importantly, you will not find someone that is trained and experienced enough to guide you in the selection process. You do not need to buy the most expensive window, but you need to understand what is important to your goals first. If you plan on staying in your home more that 5c years, the glazing is very important because the correct glazing will save you money (20-30%) every month on your heating and cooling cost. A good quality window, with a strong warranty from a company with a long history, purchased from a window specialists will save you money in the long run. In these days of rising energy prices, it is important to consider windows that support green building. Your costs to heat and cool you home in the coming years is going to rise dramatically. You may be far ahead to spend a littel more now. Interview carefully anyone you consider to install the windows. Ask them about AAMA approved installation methods. If they do not know of them and cannot explain them and how they relate specifically to your job, run, do not walk away. Lastly, get references (5-10) and call them.