Buying...Help!

Thank you guys so much. This sight is what pushed me over the edge to buy the car.
What is worse long drives or stop go. I drive it to work(15 NY miles) 5 days a week.
I have a trip planned for next week to Mass. to go visit family.200+miles. Is it a no go/ can I ride it in 3rd the entire trip? I am dead broke. I have travel money(just enough). I could prob. get the work done in Mass. much much cheaper.
The other option is worse. Let my heavy footed girlriend take my car and I take the 2002 outback. That option scares the heck out of me.
1 more question... Should i be doing preventative measures with the outbacks tranny, or is it not a problem with them. Maybe just going sinth. or somethin... Thanks guys for the help.