@Chris Sukala So it sounds like option three is by far the least lucrative deal. Listen, I'm married too...I fully understand the realities of "Happy Wife, Happy Life." But, I'm willing to bet your wife is a very smart woman (I mean, she married you after all, right?). Once you explain those profit margins to her, she probably won't like option three much anymore.
So, that leaves you with option 1 and 2. Option two looks like it needs a bit more Due Diligence. If you're going to hire out the mowing and plowing, you really need to get some quotes and factor that into your bottom line. It may eat away allot more of your profit than you think.
As for taxes, don't sweat that. Are you or your wife pretty savvy with taxes? Have you filed your own taxes in the past? My wife files ours online herself, despite having multiple properties on the books. She pays for the higher end tax software to ensure all our business expenses are accounted for but we've never taken a loss come April. We're a family of 5 with the kiddos ranging from 2 Y/O to almost 13 Y/O. I will give a word of caution though, if you're not comfortable doing your own taxes, don't hesitate to take them to a professional and pay the extra money they'll charge you to ensure they're done right. There are some things money CAN buy. Peace of mind is often one of them.