Skips, evictions, and property damage are frequent.

I would suggest skipping the program route now and read a good book or two specifically covering liens first (lets say no more that $20 total used or $40 if new).

Since we can technically answer "Yes" to the question, "Did you live in the home during 2 of the last 5 years," should we be OK to skip the 1031 entirely and just sell under IRS 523?

You will definitely need a skip tracing service IMO expect rejection and I wouldn’t mention anything about wholesaling that’s why you have the assignment clause.

Does anyone skip trace, and if so how?

1) Look for recently sold flips and reach out to the sellers and ask about their experience with the flip, and whether they are interested in buying more properties.2) Search for recent cash sales on Propstream or Batchleads, once you've identified a list of properties, you can use skip tracing tools to find the contact information for the buyers and reach out to them directly.3) Networking events can be a great way to connect with potential cash buyers in your area.Good luck!

Agreed, skip the Land Contract idea and go with a standard Mortgage.  

In the rare event that the tenant ever skipped out on paying their 30%-40% portion they could be kicked out of the program.

Like one investor says in this thread they know Milwaukee and Kenosha (skipping over Racine).

Like you said, if they're a tenant at will (I'm assuming thats a month-to-month lease), then send them a notice "reminding" them that they are responsible for snow removal for their driveway or portion thereof.And you and your wife should skip shoveling their driveway.They're in a house (duplex is SFH unit) not an apartment building.