They were more than happy to answer the questions I had gathered from everyone.

While doing that, I faced some hurdles around getting accurate economic, demographic, and real estate market data that didn't require a big software subscription and was also hyper local.

Furthermore, in terms of you stating that I'm bringing nothing to the table, that's factually not accurate.

Scott The Book on Flipping Houses,The Book on Estimating ReHab Costshttp://www.biggerpockets.com/flippingbookLocate and attend 3 different local REIA club meetings great place to meet people gather resources and info.Consider checking out HUD homes for small multi's owner occupied gets first crack.You might consider Niche or Specialized Housing like student housing.

I run them against (to ballpark them) properties that I already own in the area and I still bump them up 25% even if they look accurate on the surface.  

The reasons for this are obvious, the lender needs to know the bid is accurate and there are time limits for completing the work...generally, a contractor will complete the work much faster or at least on schedule.  

If it is your primary residence and in your own name you should be able to get very favorable terms on a 30 year fixed rate term which would keep your payments lower than a 20 year term and/or allow you to pull more cash out with a higher LTV.As far as working with the same lender (whether it is conventional mortgage lender or a portfolio lender) would be that you only have to gather all the necessary paperwork once (assuming you do the transaction close to the same time).  

The rest, it's just a choice lenders can make to be accurate and show you what you NEED to see, or mislead and show you what you WANT to see (to be revised upwards on you at the last minute).

From the information i gathered.

That way you know payments are applied properly and tax forms are accurate