I'm not sure the simulator was always free with ISE. I spent a good long time coding FPGAs without simulation and I still don't use it very often. The problem is, the FPGA doesn't stand in isolation, it is usually hooked up to something like a UART or a Compact Flash or an SPI gadget or two. It really matters more how the data is read from the CF than it does with some ginned up test bench doing a poor simulation of an CF.
The other problem with simulation is the desire to watch things happen after tens of thousands of cycles.
I llke the Integrated Logic Analyzer that comes with Vivado. I can hook up some virtual probes to exactly the points I need without having to extend signals from deep in the hierarchy up to the top level to get to a pin.
There isn't an issue with ISE versus Vivado. If you want to work with modern chips like the Artix-7, you will be using Vivado. If you want to work with the older Spartan 3s, as I often do because I have a bunch of boards, you will use ISE 14.7.
I wandered away from Altera as soon as I read the licensing terms. This was several years ago and things have probably changed, but at the tim, they could just up and cancel my license for no reason whatsoever. I went through that with UCSD Pascal and I'm not doing it again.
There are many development boards and the Digilent offerings are getting quite expensive. Even the entry level Artix-7 is right at $100:
http://store.digilentinc.com/arty-board-artix-7-fpga-development-board-for-makers-and-hobbyists/You can look one of two ways for boards: You want down and dirty with no peripherals at a low cost OR you want boards that have some peripherals. The now-obsolete Spartan 3 Starter boards from Digilent were excellent. I like development boards that bring out a LOT of pins. There's a reason that CF devices have 50 pin sockets. While it doesn't take 50 IO lines, it does take a bunch. A heck of a lot more that the 8 signals you can get in one dual-PMOD socket.
For just logic, with no particular memory requirement, CPLD boards are a whole lot cheaper, use the same toolchain and can implement logic very well. They might be a good place to start.
I haven't tried SystemVerilog but I can't seem to get up to speed with Verilog. I have been using VHDL from the beginning and it serves me well. Others will argue that it is verbose and strongly typed, which means it is harder to make a mistake, and I will agree. Enthusiastically!
Have fun with your adventure!