I haven't been the treating this like the business that it is, and feel that I have left some money on the table.

If the property isn't working for you, take the money and either re-deploy it somewhere that makes more sense, or treat yourself to a fantastic vacation!

I believe there is a time period, like 6 months from purchase to get the property financed without it being treated cash-out.

This rids myself of self employment taxes because it treats me as an employee of the S corp.  

If Trustee's Deed Upon Sale is recorded within 15 days of sale, Law of Relationback treats deed same as if recorded on 8:00 am on day of sale.

Deliver the application to their current resident, look to see what type of vehicle they drive, how well the vehicle is maintained and even if there is trash on the floor of the vehicle will give indication of how they will treat your house/room.  

But it seems I will just go ahead and sign the guy myself without further advice and treat it like any other single family home I wholesale.

Free doesn't always equal cheap :)That being said, I'd treat this like any other investment.

I've heard a rumor where a poorly written lease-option was construed as a land contract and had to be treated as such.On the other hand, a Land Contract needs to be foreclosed on if there is more than 20% equity from the purchase price, or more than 5 years from the start of the contract.On a side note; Uncontested foreclosure in Montgomery County is taking about 6 months, contested can take 2 or more years.

there's a couple of interesting twists to it. ...Vacant Land Next to Home"If you have vacant land adjacent to the land on which your home sits, you can only claim the sale of that land as part of a sale of your home if ALL of the following are true: You owned and used the vacant land as part of your home.The sale of the vacant land and the sale of your home happened within 2 years of each other.Both sales either meet the eligibility test or qualify for partial tax benefits as described earlier.If your sale of vacant land meets all these requirements, you must treat that sale and the sale of your home as a single transaction for tax purposes...."