I know boats are a financial drain, but I want to own one some day because I need a continuous project I can interact with. I live in the Pacific Northwest, which is full of water bodies to putz around or fish in. Ideally, I'd want to get something like this C-Dory here, a boat that's 20-25 feet long with a small but functional pilothouse. I don't have any plans to buy in the near future but I wanted to get some information from any idle anons.

1. If I own a boat like this one, how much time and money would I expect to invest in it on, say, a monthly or yearly basis?
2. I own a relatively new Tacoma, would that be sufficient to tow a boat of this size comfortably anywhere within my region?
3. What should I look for when purchasing a boat, are there any features or attributes that are considered "must haves" for a boat of this class?

I hope my questions aren't too vague and I can start daydreaming a little bit more. Any anons with boats that can share their experience?