Sure you could steal enough crap to reach that 1000 gold, but you would need to go in several homes. In Skyrim you can clear 1000 in most homes easily.
I normally hit my 1000 just robbing the castle or a guild in Bruma. I normally netted 3k in a couple of days in Bruma, it was how I made quick money early on. Homes were a waste of time... hit the merchants, guilds, and castles. The castles and guilds have higher risk and much higher reward.
The quest 'Bound Until Death' begs to differ, impossible to do sneakily.
Here is what you do. You buy an invisibility potion..... I have killed the bride with an arrow, then went up to her body, stole all her clothes(only wedding dress I've seen... I'm a hoarder) and my arrow while leaving a single nightshade flower, then escaped without a single person seeing me. Ok, that took 2 invisibility potions. The hardest part was actually avoiding the lizard who would start fighting everyone after he talked to me. Doing all that while avoiding him is what really took skill.