Oh, cool. Good luck!
One thing you may hit with the DB migrations is foreign key constraint errors in the community aggregates table. Or at least I did when I went from 0.18.5 to 0.19.3 (and again from 0.19.3 to 0.19.9). Basically there were community entries in the aggregates table that weren't in the communities table (or vice versa?)
But definitely be prepared to fight the migration scripts. I usually had to run the one(s) that failed, step-by-step, in a transaction and roll them back to figure out what's failing.
And once you're on 0.19.9, you can use Tesseract :P (I've got some nice mod tools you all might like).