It is a hard call.From a macro perspective the fundamentals are not really supportive of prices for the medium term (1-3 years).

It really helped give me perspective.  

Not to mention, you'd be giving up the years put into the 30 year mortgage while you were living there.Also owner occupied gives you some of the best financing available in terms of rate and down payment, so wouldn't hurt to keep a property like that as a rental.Overall, looking at it from a yield perspective, the less total cash into a deal that still has positive cashflow, the higher the percentage of yield.

I would spend more time figuring out what items need to go on what transaction for what receipt than breaking it out aftergetting a loan would be more of a pain because you would need to submit bank statements for each property for them to reviewI find that spending a couple of hours weekly/bi-weekly makes it so much easier since it is still pretty fresh in my mind.  

I worked that into my offer.My first thought was to get a fresh survey done and put up a privacy fence.The seller also told me the neighbor had previously asked to buy the property to move her mother into.  

In terms of it being affordable from the financing perspective you typically get much more advantageous terms, for example, Multifamily FHA LTV can go up to 87% for Projects with certain number of affordable units (the number of units vary based on the number of units allocated to various Area Median Income thresholds, like 30%, 50%, 60%, etc, you would also typically need a Land Use Agreement to go along with those to ensure long term compliance) or 90% for a Project fully covered by a Section 8 HAP Contract.

I had pay stubs, tax returns, and they even required higher education transcripts and diplomas since I'm fresh out of school.

Wondering if anyone has experience or insight into what % the purchase of 2 units in a spec development might be worth from a discount perspective?  

You'd likely end up with less data points but (from one random persons perspective) more accuracy.  

Solomon Johnson My personal perspective would be: pay a professional.