From what I understand, I can write off up to $5000 of startup costs from the taxes I pay on my personal income... http://www.morebusiness.com/write-off-startup-costs Let's say I start a website and pay someone $5000 to design it. Can I write that off, and if so, do I have to register the business and make the purchase in the business's name? ex. LLC taxed at sole propietor
Also, can this be done every year with a new business?
There are so many ways to think about tax laws, tax rules, and tax strategies - I strongly suggest you find a good tax adviser who will take the time to really understand your situation. In the long run a good tax guy is worth his/her weight in gold.
As a sole proprietor, you deduct that money spent from your personal taxes, and then invoice the client (the LLC) later.
do I have to register the business and make the purchase in the business's name?YES. You cannot claim a business deduction on your tax form if no business exists.
Also, can this be done every year with a new business?Startup costs are the costs associated with starting your business (for example incorporation fees). Since you only start your business once, you can only deduct these costs once in the life of the business. If you happen to start a new company the following year, you can deduct the startup costs associated with that new company.