The value added from a knowledgeable tax professional will usually far outweigh the costs.

My question is whether the reward outweighs the risk of investing in areas such as this, and if anyone has had great success in investing in Section 8.

But the differences outweigh too much, have you ever had a sub not show up on a jobsite when they are scheduled to?

Its when those two needs come together, that's when  a whole life type product may be used in such a way that there are benefits that may out weigh other investment options?

As with what @Brian Harris had to say; your potential gains are crucial to outweighing your current losses and I'm confident in your ability to get a running, educated start on a new investment in the real estate market.I'm interested in offering you a more detailed breakdown on the fundamentals of real estate investing should you wish to further verse yourself in its anatomy.

@Jered Sturm, in particular, has made some really excellent points about the merits of buy-and hold RE, but self-managing properties is a lot of work and if you don't want to be super hands-on, the stress can outweigh the marginal increase in ROI gained by doing it yourself vs working with a provider.

Forget buying real estate inside your account..there are too many disadvantages that outweigh the benefits!

He is not the cheapest guy around however the money he saves me and is able to have returned to me far outweighs his costs. 

At what point does negative equity outweigh positive cash-flow?  

Up here (look north, waayyy north), I would think the benefits of a "first-time home-buyer" qualifying for a high-ratio mortgage - 5% (two units) or 10% (3-4 units) downpayment - would outweigh trying to count a portion of the rent (arbitrarily ~0 - 75% depending on the lender) from the unit you plan to occupy.