what's wrong with negative cashflow

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I know that's stupid question.

I just don't see how I can start my first investment with positive cashflow. I would be banking on the appreciation. Is that really wrong? You gotta start somewhere right? If I can weather it through for 5 years with the cash I already have, wouldn't it be worthwhile? say 5% appreciation for 350K house for next 5 years in seattle. I think that's conservative number?

I really want to jump in, but my numbers say "I shouldn't do it." Did everyone start their 1st investment with positive cashflow?