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    <p>Do not rewrite it all at once. It is probably easiest to find a junior programmer with talent that you can bring in and invest in. If, however, the current technology is just something you can't continue using (that happens, especially with proprietary choices, but even in non-proprietary), then transition in small parts.</p> <p>First, realize it doesn't matter what you write it in, if you don't have the in-house talent to maintain the thing from people who know the software, having someone who can maintain and grow the system will always be a problem.</p> <p>So bring in that someone who will own and maintain it. If for some reason you can't get someone willing to work on the proprietary platform, get someone who's job it is to transition to the new platform (whatever you choose to use).</p> <p>Then peel off parts from the old system and redevelop just that part - and this is the most important part - put that part in production before moving on the next part. This has two advantages. First, if needs change in a different part of the system, you can still maintain it without impacting the scope of your new project. Second is that all of the little details that have to be fixed come in manageable chunks instead of having a massive overbudget project that grinds all new development to a halt.</p> <p>And a final piece of advice - if you decide to ignore all of the above and rewrite anyway - make sure that your rewrite adds no functionality over what the existing code does, it just repeats the same functionality as the current application. That way you won't get lost in all the new requirements everyone is trying to cram in.</p> <p>One last thing - don't ever, ever outsource this kind of effort - you will regret it. Two things will happen. The first is that it will go massively over budget. Consulting firms in this case are basically guaranteed to underbid. The second is that at the end, you won't know the resulting code or architecture well, which will put you in exactly the same position you are in now.</p>
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