When buying or selling a website there are many factors to consider that will ensure a smoother transaction. While "buyers should always beware", following a few simple suggestions could avoid problems later. They are presented in no particular order.
Will the seller offer any assistance or help after the transaction is over? How much of your time, effort, know how will maintaining and operating the site require. Do you have all the technical as well as creative skills to maintain the site?
How long will the owner stay at the site and train the buyer in running and maintaining the site?
Make sure to closely look at any Profit and Loss (P&L) statements. Try to look up at back-up documentations such as tax forms, banking records and other information. It is always a good idea to have an accountant or CPA review all the information. Accountants and CPA can also advise you on any possible tax consequences involved in such a transaction.
Like in any transactions, whether you are the buyer or the seller of a website, it is important to have an agreement with the other party. The agreement should set forth all the terms of the transaction. Try to provide for all contingencies. You can find useful forms for buying and selling website here.
It is advisable to use an escrow for the transfer of the website and the domain name. There are several online escrow companies that can assist with this kind of transaction. The escrow company usually chanrges a small fee (based on the total dollar amount of the transaction) to assist with the deal.
If you plan on keeping the site you are buying with the current hosting company find out what their current service offers and if they offer any other services. For example do they offer good technical support, programming services, available libraries of software to use on the site, other tools, statistics packages etc..
Figure out if there are any technical issues involved with the website you are acquiring? If you don't have the technical knowledge, you will need to find someone qualified to look "under the "hood of the website" and make sure that all programs and databases are fine and that everything is in order with the site from a more technical standpoint.

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