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I think your idea on the math is flawed... If you priced it at $500/$99 and end up with 10 users that is $5000 now and $1000 a month.
If you did it at $200/$89 I am sure you'd end up with 18 users at $3600 and $1602 a month. After three months you are at the same spot and from there on you are making more than you would have before. Not to mention you can then offer specials, etc at that point to entice others to get in on the $89 monthly and increase that user base to 50. At which time you can offer a price drop across the board of $100 setup and make all new users $99 a month and grab another 20 users...
Gives you $2000 bonus and another almost $2000 a month...
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