I can see there's a lot of good advice in the comments. I just wanted to contibute my 2 cents to the matter. I've done a lot of conversions, interconnection of

I can see there's a lot of good advice in the comments. I just wanted to contibute my 2 cents to the matter. I've done a lot of conversions, interconnection of disparate systems, migrations, monkeypatching and straight abominations in my day. In your position I would hire senior freelancers to patch the system in interations. First, fixing the most anoying issues you have in order to streamline the whole process. This will allow the programmers to really understand the domain and based on that knowledge iterate and consolidate pieces of the architecture until you have what you're looking for. I don't really believe in complete rewrites or starting from scratch based on my experience. Most of the users/companies I've dealt with (small and big) don't really have documented processes and domain knowledge. Well, that's not fair. It's rare those are documented and up-to-date. That's better :-) I agree with some of the comments, the technical challenge is what attracts people (at least that's my case). If you're looking for people to tackle something like this, please send me an email :-) Cheers.