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Legal Action - Ask your Boston web design company if anything on your site could result in legal action. The last thing you want is a lawsuit or some other legal problem over your web design so find out in advance if this could be a problem.
Bandwidth - Using design methods like CSS or XHTML means you will save a lot of bandwidth; your site will download several times faster not to mention that you will save lots of money. So, make sure you ask your web designer what type of bandwidth will be used by your site and if CSS or XHTML are options. Your Boston web design company should be able to handle any of these and will let you know what will be best.
SEO - Search Engine Optimization is incredibly important and you will want to know what Boston SEO methods are available for your site. Basically, SEO means that your website content will be written in a manner that will help it rank higher in the search engines and get more hits. Find out from your web designer if the content is written by an SEO expert or not.
Upgrades - You will also want to find out if it will be easy to upgrade your site or not. The easier your site is to upgrade the better off you will be. So, consider paying a little more up front and having an easily upgradeable site that will save you money and time in the long haul.