I want to find a short list of properties and actually start running the numbers on them for real instead of the quick benchmark calculations.  

Service contracts are key, and I'd recommend getting a detailed, itemized scope of work included in it, along with benchmarks required prior to subsequent draw payments. 

Any tips on numbers I need to garner, cash-flow benchmarks I should obtain, and general Land Contract experience (not something I have dealt with as a licensed real estate agent) would be much appreciated!

When you have a larger portfolio, you expect more for your money.2% is just an average benchmark.

Such as what's a good benchmark for cash flow on those types of properties.

So maybe the #'s don't look as appealing, but their is certainly demand and with high occupancy rates, that can offset being less then 1% which seems to be the benchmark.

I am a real estate agent/investor with Benchmark myself, but instead of recommending myself I can give you an awesome referral. 

It's called a 1031 exchange which refers to Section 1031 of the IRC which states: “No gain or loss shall be recognized on the exchange of property held for productive use in a trade or business or for investment, if such property is exchanged solely for property of like-kind which is to be held either for productive use in a trade or business or for investment.”To be clear, there is a process and time limits on when benchmarks need to be accomplished to qualify.

If predictable appreciation is in the cards, that changes the equation but I would still recommend bench-marking it relative to other investment properties.If you are willing to house-hack as you mentioned with the duplex, that is an excellent way to get started in REI.  

I'd recommend calculating your future expected returns for both types of properties that you are buying, include appreciation, and bench mark them relative to one another.