We just pulled the trigger on a 2015 Outback. Im the same size and we have much the same uses.
Regarding new vs used, There was a used one in craigs list and it was on the table for purchase until I spent a night on the forums. I read the comments on the new seat and it was the clincher for us. Keeping a dry bumm, being way more comfortable on long rides, and having the options to do about anything was what we were looking for. We have a lake cottage so everyone under the sun will be using it from kids to grandparents. The sail arrived today, sidekicks and big rudder are on order. We have canals to explore and islands to sail to as well as musskie begging to be caught. By the way, One thing that is not real clear in literature is that the 2015's come with the turbo fins as "standard" (blue 13 tooth for the outback). That helped too as its a upgrade that is already done for us.
One thing I found that I wish I had found before purchasing was the posts about primary vs secondary stability. Search for those. They are a very interesting set of posts. I always figured wider was better for stability and it is but..... it is also the worst as well. Just depends on what is likely to cause you to tip. For me its a speed boat zooming right past me as I sight see or choppy water as I cross the lake. For those issues I bought the wrong boat, I should have gone narrower. For the wobbly footed though we got the right one. The outback wont likely be tipping because of anything I do that's for sure. As for the 200hp idiots that zoom past me 20 feet off my portside, that's where the sidekicks may come in handy when I least expect it.
Best of luck choosing and for sure try to get in one to try them out. They make all the different models for a reason, one size does not fit all.