We would like to present 3-5 owner-financing choices/alternatives for him to select from.Does anyone have experience coming up with choices that vary along term, interest rate, purchase price, percentage down, etc.?

He is now a nuclear engineer working for the Navy.

What are other alternatives to find motivated sellers?

Alternatively keep the condo and renovate it to max out on the rent.

I am not aware of any easier way to do it, since you have to prove that the property is eligible, meaning someone pays a utility in the building; I took the easy way out, so I didn't even have to check whether there was an alternative.

The alternative is to sell my current residence, use some of those funds plus my current savings to buy a rental property + new residence.

Alternatively, you don't have the increase to her portion, if you want to retain her. 

I assume they aren't cool with that, because if they were you wouldn't be seeking alternatives.

But I plan to contribute to life insurance anyway as an alternate way to transfer wealth.

Your time and efforts have value, and if you gift such value to the IRA by performing services, you are effectively making un-documented contributions to the IRA and artificially magnifying the tax sheltering, which is why this is prohibited.The alternatives in the NPN space are to joint venture with other parties or use some kind of a note broker who is doing the workouts.