$3,000.00 is a good price to pay for a first boat. You're going to end up spending money - regardless of what boat you buy. Even with a new boat, there is always something that you need (or think you do). Roughly, you can expect to sell a used boat for what you paid for it, if you maintain it. If you make it beautiful, you'll get more than you paid for it, but keep in mind that it will always be an old boat, and there is a certain range of prices associated with any given model year.
You will not recoup all of the money that you spend on repairs. And how much you get back depends entirely on whether someone falls in love with it or not when you want to sell.
As far as the specific boat goes - I will probably get pooped on from great heights for saying this, but there is not really a huge difference between the 23 and 24 foot volume production boats. There are some character boats out there for sure, but generally Pearson, O'Day, Bristol, Ericson, C&C, etc. are all decent starter boats.
If you're looking at larger boats, then this 23 is probably not a stretch for you - which is a good situation to be in. You can refit here fairly well, have some excellent adventures, and not be boat poor. Good luck !