Tried playing through New Vegas about 3 times now and failed miserably every time. This most recent time due to the game constantly crashing. This has happened both on Win 7 as well as 10. You guys have any suggestions?

Yes, I do have some suggestions. New Vegas is one of my favourite games and I've managed to reduce crashes to once every 50 hours or so. You see people claiming to run it without any crashes but that's not really possible.

The trick to enjoy New Vegas is to use mods. I prefer the vision of developers, i.e. the "vanilla" version, so I only use mods to fix bugs and improve the graphics. You can get mods from nexusmods and there are plenty of tutorials for installing these. It might take you an hour or two the first time.

I recommend these mods, in order from most important to least:
- NVAC: New Vegas anticrash uses the power of assembly language to fix some nasty engine bugs.
- NVSR: the stutter remover makes the game smoother and also fixes some bugs
- YUP: the unofficial patch fixing hundreds of issues left over by the developers.
- Ogg vorbis libraries: upgrades some old open source libraries
- Optional: NMC large, character overhaul and ENB: doesn't fix any bugs but improves the graphics.

Let me know if you need help making sense of all these abbrevations and terminology.