Lynyrdsky1,
I have been following your posts on this for a little bit and have yet to comment. Let me say a few things to you. 1 you are a young guy and you seem to really think things through from what I can tell by your posts. I would give you this advice because I have been there and done that, made some really bad decisions and put myself and my family in a bad spot due to my desires.
Figure an amount that you think you can afford, cut that by 30% to 40%. Things always come up. Stuff breaks and needs to be replaced. You may have to save longer to get what you want, but fiscally its the smart thing to do. The costs associated with owning a boat do not come down what you see in front of you. Figure anything and everything that can happen will happen ( Murphy's law) and they do.
To me it's a toss up. Buy simple and upgrade as you go and as you can afford it, or wait and sve until you can afford exactly what you want. No matter what you have it will get old after a while and you will want more. I am not trying to discourage you from getting what you want, but I have been in your shoes ( a young guy) made some bad desicions and if I can pass anything along to anyone it will be to always think ahead on big purchases.
Good Luck.