My honest opinion is that if you are serious about developing a site that will generate (hopefully significant) income, then you should be serious about having your site professionally developed. If you are creating a payed service for people, then you need a site that is both reliable and very secure, and that can only be created by somebody who has years of experience in advanced web development.
I know you have a concern about costs and funds, but if your plan is viable, then you should be able to have access to either investments or funding/financing.
Please take this as constructive criticism, coming from past experiences and witnesses. If you are only proficient with the daily operating of a PC and haven't yet grasped the concept of HTML, then trying to do this project by yourself will only lead to failure. On the otherhand, if you have lots of time and patience on your side, then there is no reason why you can't attempt your project. But if you want something that can generate income (I mean serious income as opposed to Google adwords on a blog), a reliable and secure service for customers, in a reasonable timeframe, then I think you should seriously consider getting your site professionally developed.
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