Using that metric I can predict with relative accuracy my CAP, COC and cash flow.

Obviously there is more to maintain (three roofs instead of one, more exterior and interior wall surfaces for painting, cleaning, more soffit vents, more piping, more of something to go wrong), and also the maintenance is non-standard, as each cottage has it's own unique plumbing, electrical, AC, ducting, sewers, water supplies...versus in a standard 4-plex all the units have "similar" layout and the issues are more predictable and less challenging.These cottages are not on a very large lot that can be subdivided in the future.Would you ever consider buying multiple stand alone structures like this if there is no price advantage versus a 4-plex on a per door basis?

I can't  predict  the future.  

Your realtor is pretty bold predicting the market will come down next year.

By investing in this deal, unless you plan on losing money, you are essentially saying that you are confident that on your first flip you can predict all of the costs, timeframes (and effect that has on costs), scope of work (and effect it has on cost), performance of your teammates (and the effect that has on costs), and exit price within $10k on a $365k investment, or within 3%, on your first time out of the gate as an investor!

If you are trying to predict for the future you can't.  

I would add that no landlord can precisely predict the time factor of a property. 

What is your prediction for that market in relation to the recent oils field bust?  

If everything in my personal life stays the same (of course no one can predict a Black Swan event) in terms of W2 and if we hold for a while, are there any outside factors that could be that severe that we'd be forced to sell?

You definitely aren't going to have a great predictable return, especially in the short term, if you try to invest turnkey; at least at the single family and small multi-family level.