I am an assembly beginner who migrated from C who is interested in making yet another floppy boot sector os. I guess you can say I'm not satisfied simply playing in someone elses sandbox and have the goal of making some kind of os by fumbling through it head first just like I have learned everything else.

I know there is a large list of emulators that exists out there, but they are somewhat unnewb freindly and you really dont know whats going on under the rug.

Im using emu8086 as an example, its a emulator packaged with an assembler that emulates intel 8086 real mode.
It has a gui showing the machine code, registers, stack, as well as the entire memory contents. When you run your code in emu8086 you can see everything with your own eyes and slow it down or pause it. You can actually see what register value it was that you did or did not set for example that caused the error you didn't expect. When I use any other emulator without these features and something goes wrong I'm left staring at the screen with some rediculous expression on my face.

If I'm going to make any serious attempt at making an os I'll need tool for at least protected mode x86 - which there is many available, but none of them are like emu8086.
I'm probably not really ready to start making a long mode os yet (still making pong and tetris clones in real mode and making my own dos clone) but it shouldn't be too long before I read enough tutorials to start digging my way back from the retro days of 1980's era computing.

The tools of choice at the moment would probably be qemu or bochs.

VirtualBox and the free version of Vmware would also be good tools.
Some of these emulators also provide x86-64 mode, which, if you've got the processor means that when you stick it on your hard disk you can run it with all the advantages.

Hm, how does VirtualBox relate to BOCH and QEMU? Does it use code from either, or is it 100% new code?

Yea but I was hoping to find a 32/64 bit look-a-like to emu8086, most other emulators aren't very newb friendly and they don't let you visually see what is going on while you emulate your code (as in show the registers, stack, and other memory in a little window) and allow you to pause or slow down the execution so you can debug problem spots.

When I can't see whats going on in the registers and memory I feel like I am poking around in the dark.

QEMU has a built-in debugger afaik - probably not as close to emu8086 as you'd like, but worth a shot...

As far as I know it's based on qemu with new interfaces, kernel modules and just a forked version of the qemu virtual machine