So starting to really think I need to get a boat and just sail over doing all these courses, but being a full time student, money is an issue.
How did you come to take ownership of your first boat, and what do you suggest for someone looking to get their first? (Still want a contessa 26 or 32)
As a student you may have some access to student body sailing clubs, which are the best deal around. The one associated with a local state college has student memberships that give you a year of unlimited access to boats for less than what I pay for a month of moorage.
The boat isn't the expensive part, you can easily find a 1970s 20-25' boat in safe enough condition to enjoy for a couple of thousand dollars or less. Frequent examples in Seattle would be Tanzer 22, Catalina 22, Santana 20, San Juan 24. The problem is the ongoing moorage costs. I'm going to guess that if you don't think you can afford the boat that moorage is going to be the real issue.
At my old marina (maximum boat size of 27') most of the boats were purchased for around $3000 or less, with the cheapest being $200 (but I didn't consider that boat safe) and the most expensive still being under $10,000. However everyone still had to come up with $2000-$3000/year for moorage.
The only way to make moorage cheap is through living aboard, and that has a different set of tradeoffs.