As a recent college engineering grad who formerly had only been exposed to the typical American life (piling on as much debt as possible in hopes of keeping up with the Joneses), you guys have really got the gears turning in my head and have opened a new way of thinking for me.After recently obtaining a good paying job, I almost made the mistake of buying a new truck and taking on some of the other bad debt that comes with most college grads; instead, I have chosen to put my eggs in the real estate basket.

. - what will you do, if one year after you sold your flip, you are getting sued by the buyer because of some defect or issue, real or imagined, known to you or created by a sub/contractor, or fraud (like, because you made the mistake to advertise your flip for sale with "everything new" and the buyer discovered you didn't change the entire plumbing) and the judge freezes all your bank accounts till things get sorted out?

The worst he will say is "no" and you either take it as is, or walk away. 

Am I setting myself up for failure by not always putting in worst case scenario?

At first, I made the mistake of being lenient and waived several late fees.

Worst case scenario yes we need to have someone else do it. 

If you've gone abroad recently you might be ok but I made the mistake of not keeping my eye on when I would start to have to bring things onshore.

This is an area I believe not often explored and has led many to waste a lot of time waiting to refinance or worst waiting for appreciation, while great cash cow deals pass them by weeks after weeks, months after months, years after years. 

Fortunately, I learned another valuable lesson about a month before that the worst thing you can do is not at least ASK for something, because the worst someone can tell you is no.

This was my worst case scenario analysis, and I'm okay with it because the house is under market value and in great shape and it's already tenanted and it gets me into the market, but it does mean that I'm making about $150 negative cash flow each month.