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If you anger the SE's, on one then all is not lost. Take a different tack on each site. It will both keep you busy and you will be able to judge what is and is not working.
I personally would diversify industries and especially income sources. As one industry changes you are covered and as one form of income (eg. AdSense) changes, you will have others.
Plus if one or two of them take a hit you don't lose 50% to 100% of your income in one hit, but more like 10% or 20%. I can do much better at rebuilding if I still have 80-90% of my income than 50% or less. In addition, like the stock market you never know for sure which ones will do really well and which ones will tank. Diversifying your businesses will help insure against "putting all your eggs in one basket" as it were.
Now as another poster mentioned, diversity can be difficult to do as you have to juggle multiple balls at once. I try and keep my streams closely aligned or at least complimentary to each other that way work I do for one can potentially be tweaked a little and used for another instead of having to develop everything from scratch every time.
There are a number of great books written about this concept, some out of print, but most them can be had from Amazon used or new.
Look at my nick!.......It is all about playing the percentages!
Since 1999 I've believed in diversification!
Some of my sites are white hat, some are black hat, some are middle of the road, some are controversial.....you need to check your personal morals at the door to make a lot of money in this business :)
In 2000-2004 black hat (by today's standards) made a bundle....now white hat is doing better and black hat are declining......you have to move with the times, and who is to say it won't change back again at some time in the future?
"Black Hat" sites are those typically described as cheating and spamming seach engines for so called "Free Exposure"!
Instead of paying for "Sponsorship", Black Hat sites generate artificial ways of getting to the top of free search terms.
Always remember that "Bums on Seats" is the number one rule of marketing to the mass public.....if you can achieve that for "free" then you can't lose!.....of course it is not really for "free", a lot of work is involved in producing a site that avoids paying SE's!
"White Hat" sites achieve the same results without using the "dirty tactics".....that is basically the same thing.....but much more work!
The subject matter of the site doesn't matter that much.....although high volume sites are target "Black Hat" sites for SE's. And has to be done manually as there is no way they are catching these with a program!
Right now, my advice is to "play fair".....In years gone by playing "dirty" worked better.....but, at the end of the day the ability to switch is what counts....and for that you need a lot of ready-to-go sites!
It isn't something complex.....it is putting a lot of irons in the fire and then using the ones that get hot effectively......there is nothing new in this concept!
If you put one iron in the fire, and I put a million, who has the best chance of pulling out a winner?
The beauty of the web is that you can bet on all possible winners!