Just a little on painting...
Do a good prep for the painter, strip it... don't prime it....or just strip the old paint layer off and old primer (unless you have a good eye and can see smoothness). If you try re-priming the paint, the primer chemical make-up might not match what the painter uses, so he/she will have to strip it anyway.
When talking to the painter about your bike ask him what kind of jobs he/she has done and do they have pics.... a really good painter will say...yeah I've taken a few pics but haven't really posted them (put them in a book). The ones that like to brag about their jobs usually don't like to paint a "plain" color and charge more. Oh and if their shops is a mess and they are only asking $100 bucks....walk away, more often than not you will get what you pay for...even if its ol' bob who has painted for years...the percentage of "clean vrs dirty" is on the clean side.
The high-school/tech-school is a good idea... lotsa those kids are there for a reason, they love painting, you might get a good custom job done on the cheap...at cost only, if its cost only ask how many kids helped, if it was only a couple tip them...make them want to do more.
Last but not least....don't forget the underside...always put a good road coating on the underside. Reguardless of if you are up north or down south a good undercoating will save a lot of cleaning and rusting later on down the line.
And that's my 3 cents..... thanks for listening