Please excuse my long-winded explanation, but I wanted to be as explicit as possible in the hopes of getting as much useful feedback on my situation as possible. You can skip to the questions at the bottom if you are impatient.
Explanation
At my current job, development is done in an antiquated language that is hard-wired to a proprietary DBMS that comes with the language. The language is CRUD-focused, and is essentially a glorified database querying/reporting/updating language with some programming features bolted on as an afterthought. Most programs are top-down procedures and there is very little code reuse; updating a record often requires updating many entangled, related records at the same time that you just need to "know about" as the proprietary database has no inherent foreign key relationships. If a table needs to be updated, we generally must grep our source code and update every procedure that creates/updates records for that table and recompile. I could go on with other annoyances, but needless to say, I am looking for a way to abstract away as much of this behavior as possible into reusable code segments.
The language has semi-recently added some support for object-oriented development, and I have been able to demonstrate the benefits of reusable code to my coworkers with a recent project written using OO constructs. However, my project was only possible because it was a rare task that did not require interacting with our database.
I have really been trying hard to find a way to create re-usable code using OO techniques with this language, but since everything is so database-focused, what I really need is a way to create container classes around our table designs, putting most of our data processing logic into class methods and merging N related tables into 1 singular class. This has brought me to the idea of ORM frameworks, which of course is non-existent on the language I am using at work.
What I have found, is that the DBMS for this language can run a SQL99 engine concurrently with the proprietary language engine, and it includes JDBC and ODBC drivers. This has opened the door for me to explore migration strategies, which is where I think we eventually need to go. Since the SQL engine runs concurrently with the old engine, it is possible for us to do an incremental migration, running new code alongside old code with an eventual goal of migrating our data to a "pure" SQL DBMS when all the old code is replaced.
I initially did quite a bit of reading and proposed Java (using JPA2 for ORM) to my manager, but I think I scared him as he views Java as being a bit heavyweight for our needs. I then did a little more digging and re-proposed Ruby using the JRuby interpreter (using either ActiveRecord or DataMapper for ORM), which was much better received as Rails seems to fit in well with the re-shifting of our development to Web-based front-ends that we are attempting to move to with our old cludgy code, and of course because the ability to interact with Java if the need arises is a great capability.
The Questions
Nearly all of the reading I have been doing about ORM is focused on starting with a class structure, and creating the mapped database structure as a secondary process. Is going the other way around (starting with an existing database and mapping classes to it) a very odd thing to do?
Assuming question #1 == true, how flexible are existing ORM frameworks such as JPA2, ActiveRecord, DataMapper etc. to "imperfect" table design? I am sure we will have to do some refactoring of existing table design, but would like to know if I am undertaking a Herculean task before I waste too much time on the effort.
If anyone has a better idea for language+ORM, I would love to hear it. It must be SQL-ready using JDBC or ODBC to fit into our incremental migration plan.
If anyone has any experience on a similar effort and could point out any helpful resources (especially books), I would be very grateful!