Since my strategy is to live in the ADU myself so I can rent out the larger space, I would definitely want it to be fully functional with a kitchen so I can feed myself = ).

I've done this through:1) hands on work on my properties 2) working as an accountant for construction related companies which allows me see all kinds of cost data and learn how things are done through performing my job function 3) Taking on non accounting duties at these construction companies such as labor, estimating, project management4) Taking construction classes5) Reading as many books/articles as possible6) etc I expect to get my contractor's license in the next year or so.

Also there is a search function top right, If you type in private money you should find a number of links on raising private money that you might find useful. 

The overall "feel" of the property...this is somewhat subjective, but some houses are incredibly well-designed and have great aesthetics, floorplans, and functionality...other properties are poorly-designed, lack aesthetics, have awkward floorplans and poor functionality.

Otherwise you’re going to have to use the ‘draw” function to search comparable and then do $/sf.  

With #2, I either get a bunch of PM functionality I don't need, or I utilize the PM functionality by re-entering a ton of data every month that was already provided to me by my PMs.

The buyers got a much better, more updated and functional home. 

So even if it feels premature for you, I’d start right away looking for an excellent PM, or else a partner who might fill that function for you!

better off not operating an STR or any property functioning on schedule E from an LLC or an SCorp just do sole proprietor you’ll get better tax breaks.

Except for the emergency room staff, who may or may not be hospital staff (they may rotate into the ER from their private practice), doctors are generally in private practice or belong to a larger office of physicians with admitting privileges at a hospital so they can use the facilities to perform operations.Also, you speak about the Affordable Care Act in the future tense.