Multiple Streams Of Income vs. Eggs In One Basket

Not sure I'm alone here, but I've had this "problem" for the past 5 years. I got extremely lucky and hit a home run with my first site. It generates lots of revenue, I have consistently improved it, and it launched my career selling stuff online.

But being a conservative person, I wanted to have some more legs to the stool. So I first decided to build more websites and kind of spread out my time. I built some adsense sites, affiliate sites, and more ecommerce sites. All in all, the sites combined do pretty well for the amount of time I spend on them (zero).

I think my neglect of other sites gives me anxiety or guilt or something. haha. Because every year I say "This site has been making $1000 a month and I haven't done anything for 3 years, imagine what would happen if I spent some time/money on it". Then I start, and then I fade out because.......

I usually come back to working on that first site that's the big money-maker. So to give me the feeling of diversification, I have just expanded the channels that I sell. Instead of just relying on SE traffic, I do lots of PPC, I sell wholesale, I dropship, I started an affiliate program and pay out generous commissions, etc, etc, etc.

I feel a little better about the strength of the original website now because it's been growing for 5 years, but it doesn't take away from my underlying frustration that I haven't been able to come up with a process for outsourcing the continued development of these other sites.

So I'm sure I'm not alone right? How do you guys deal with these websites you develop but can't devote time to? You just sit back and collect the check?

Or if you outsource, do you just write down the steps you take to promote a site and then piece that out? Or try to find a person to handle all of it?