Although we'll be losing a good chunk of cash in doing that, our "debt to income" ratio will no longer be a factor (negatively) and possibly get us better loan conditions.

if it goes fine alls well if it gets botched the first one to lose is the junior position..

They pay the mortgage and my utilities (essentially living and owning a home for free - in your shoes you would be cash flowing).Then, depending on what you are doing for a job (or college), it'd be good to establish yourself at work and save enough for your rainy day account (savings in case you lose your job) and then start saving more for a rental property.

Where is the best site to view these type of house plans?

If it isn't directly next door, I'd say provide the W&D, or you will lose business to someone who has one on site.  

That being said, you reiterate numbers that you can accurately portray and stress your worry as you do here in potentially losing the investment opportunity.

I would also do what Tasha recommended by using Zillow or you can use the county assessors site to see what the area is selling for.

I'm a big proponent of using sites like homeadvisor, thumbtack, porch, etc to find contractors, but for the life of me I can't seem to find a decent contractor to do drywall finishing or stucco a project that we're completing. 

I honestly don’t recommend this for you just cause you don’t seem experienced enough to successfully pull this off and the downfall is wasting an investors time, whatever appraisal will cost you, and losing an investor with tons of possible future deals because you bit more than you can chew on your first deal with him.

As a result there is a very real danger that hosts will be penalized, receive bad reviews on social media, and even lose their accounts on Airbnb/VRBO which could quite realistically cost them their businesses if no consideration is given to grandfathering in owners and hosts who are already operating more than one STR per lot, not to mention it seems fair to give owners and tenants a chance (as was mentioned) to recoup their significant investments (as one neighbor mentioned--her life savings) which they made under the existing laws."