After a few weeks of looking at Sacramento properties and crunching the numbers, I've been wondering the same this myself. 

I do think being a broker, contractor, or even a property manager would substantially help you, but at the end of the day, its about crunching the numbers correctly and being realistic.

If you've crunched the numbers and after all foreseeable expenses you're cashflowing $800+ per month, then the negative equity is not a big deal.

Crunch numbers on listed properties and make some offers.

You don't get the rent you were hoping (always be conservative in your number crunching)Make sure you consider these holding costs in your numbers and give yourself deadlines of when the rehab MUST be done by and when you MUST rent it out by to hit the numbers.Might I also suggest running your numbers through the BRRRR calculator?

I should also be able to accelerate paying off the 401K loan in Nov with my annual bonus (not a guarantee but pretty darn close).What I'm wrestling with is, do I take the short term crunch on cash flow (anywhere from 6mos to 2 years) in order to get into this deal.

Whether you learn to do the research yourself, delegate it or outsource it, there is a certain amount of risk, especially when in a time crunch. 

Even when I've crunched the numbers, there are always doubts about the variables of a property.

They can walk out the door with a professional product and more crunched numbers than they care to look at.

The recent bail out has pushed these predictions to further speculation considering the crunch tax payers will now have face.Someone here posted that he believes we'll post double digit inflation in our future and it goes without saying, this is the sad truth.