instruments
From a circumnavigation using a sextant, stopwatch and RDF to navigate to cruising the Caribbean today w/ a chartplotter networked system (radar, depth, speed, weather, etc.) is a long long trip.
I have had many great relationships with Garmin products. Raymarine; not so much.
So I'd suggest a Garmin chartplotter within your price range. Radar if you feel you need it can be networked in & shows up on the plotter screen (great not to need a separate display). If you sail a lot, I'd highly recommend the xm-weather unit for the Garmin network; it's just like having the weather channel radar aboard plus audible & visual weather warnings.
As for wind instruments, I think they are a really nice addition to any sail boat & would try to include them. I am going to try the TicTac wire-less units when my ST-60 gear fails. For the higher price you do not need to run wires up the mast or to the cockpit. Though I've not had one yet, I've heard nothing but good about them.
I find it is beneficial to have a thru-hull speed indicator to get the current by comparing boat speed to GPS speed.
I have both 7" & 10" screens on the Garmins (10" in the cockpit & the other in the aft cabin to monitor the helmsman's precision & quite frankly the larger is better. Again you have a budget; better a smaller quality unit & some networked additions than larger screen alone.
I am not in the market for new electronics yet (not soon, I hope) so I'm not up on model numbers. But the above info should cover several lines of equipment. Always look for the latest model of discontinued electronics for the best deal. I would not recommend used, though.
Lastly, we find our autopilot indispensable. It's another crew member that you don't have to feed, live with or listen to; it just does it's job. Eight hours on the wheel can be FOREVER!
Good luck & great sailing.