Mold is part of flipping it just depends how bad.

I know it depends on what it looks like inside, but does this spell disaster or extra future expense?

It will all depend on the home and condition.

It all depends on your goals.

@Kyle Marek I think that depending on where you are (close to the rail lines in SD, ocean, downtown) you could do much better renting by the night than by the month.

As far as the negotiations, it sounds like you are taking a good approach, I just finished the audio version of "Never Split the Difference: Negotiate as if your life depended on it" by Chris Voss.

I think it depends on your overall goals/objectives.

Depending on the length of time you can look into an FHA loan since you will be living there (I do not know the time you have to hold the property for).

The deal I'm negotiating right now has an estimated cash flow of $150-$200/mo. depending on how the numbers fall in the end.

I would say it depends a lot on where you are located, if you are in a resort town in Hawaii or somewhere exotic it could take a greater hit.