Upgrade or Alternative Solutions

[viben]

My entire electronics package is Raymarine, except for the VHF radio. At the center is an E90W hybrid touch screen, accompanied by radar, autopilot, and the usual wind and tridata for a sailboat – all from when the boat was new, a little more than 10 years ago.

I am now considering my options – upgrade or not – and have several questions:

1) Can I upgrade the chart plotter to any of the new, wifi enabled ones without having to change the rest?

2) Can I install a new AIS transponder (don’t have one now) and make it work with the current system?

3) Can I update the chart platter software to the latest on my current chart plotter, and if so, how do I do that – via CompactFlash?

4) The recent upgrade to Windows 10 made the RayTech navigation software useless. What are my options for similar?

5) Is there a way that I can import routes (waypoints) from the Android Navionics app (.kmz files) to my current chart plotter?

What would your recommendations be?