With each passing year, I become more conservative and love investing for stable cash flow rather than gambling on appreciation.

You'd be gambling that you found every billable issue because you know that you'll never see that money again once it walks out of the door. 

If they don't, they are behind the curve and you are gambling that when they do get caught up that it might not be in your favor.Good luck!

So, that sounds like a huge pain, though it's probably pretty straightforward and only a handful of documents, but man it makes me feel like just taking a gamble!

Not to mention that anticipating appreciation in the model is basically educated gambling.

i want to do what has the best success rate . the stock market just scares me . i feel like im outside a casino watching someone else gamble with money and i have know control . that money didn't come easy . if i could get it out with out the huge penalties i would have done so years ago .

It took a gamble by accepting cc payments that a tenant would later dispute the charges.

Therefore, it would really just be a gamble on appreciation.

Fantastic returns, just don't check your brain at the border.

Now, you as the receiver of the 1099 will pay SE taxes, so if you are also the owner of the S-Corp the whole situation is tax neutral, but the IRS will still come after the S-Corp for not following the law.Issuing a 1099 to the owner of an S-Corp could also be border line fraud.