I’m thinking about registering a sole proprietorship for a small business. When registering the company in the country, would it make sense to name it with a .com extension. In other words, say my company is called Darryl and I’ve already registered the URL www.darryl.com, should I register the company as Darryl or darryl.com?
I don’t think there’s a GQ answer to this. To a large extent, the DBA (doing business as) or trade name of your business is just what you want to put on your business cards, phone book listing, etc. Your legal name can be totally different from the DBA. I often recommend that people stick with generic legal names (Darryl Enterprises, Inc. or something) and then set up a DBA for what the customers will really see and remember. It’s usually easier to update a DBA than a legal name if you ever need to.
Including the .com does help make sure people know to go check the website.
The .com in the name implies that you do business over the web, so it might not be a good choice if you’re a brick and mortar store, a caterer, or some other localized business.
The presence or absence of the .com will probably not make any difference in trademark or licensing issues, but you’d need a lawyer to analyze any close calls.
If you register as Darryl.com, people are gonna be disappointed when they try to go to Darryl.com.com 
Thanks dracoi.
I guess one of the things I’d like to sell are silkscreened t-shirts. I’d like to protect designs by using a ©darryl.com on the design. Would this give me any amount of copyright protection even though the company is actually Darryl? This would automatically direct people to www.darryl.com if they happened to see it on a t-shirt.
I am also understand it will give me a greater degree of protection if I trademark the company name. Is this true? How do I go about doing this?
Since this is a sole proprietorship, could I also run my condo rental income through this entity? Should I just maintain a separate checking account for the real estate?
Ah, I see that I register trademarks through the US Patent Office, so that question is answered I guess.
You own copyright as soon as you create the designs, whether you register it or include the copyright symbol at all. Registering the copyright can help with legal damages, but may not make much of a difference for the typical small business owner.
I think you found out the steps already. It’s a good idea to get an attorney’s help in drafting the trademark. Part of the process is the research to establish that you can trade mark a name at all. Remember, the owner of the trade mark is the first one to use the mark in trade… not necessarily the first to register it.
Legally, you can do it any way you like. For the sake of bookkeeping, tax preparation, audits, etc. I would strongly recommend separate accounts for each activity.