As an aside I am a surgeon with a high W-2 income but less available time due to a demanding job.  

Looking for examples that qualify or examples in these 11 categories below of “real property trade or business is any real property trade or business that is involved in:” - development, redevelopment, - construction, reconstruction, - conversion, - Acquisition, brokerage - Rental, leasing - operation, management, Trying to gain a more clear and detailed understanding on that part.

A cardiovascular surgeon three states away has no interest in calling Ruby to find out if she can clean the cabin on Friday instead of Saturday, or calling Joe Handyman to see if he can get over and fish a snake out of the dryer.  

Here's the issue: (1) the house needs repairs, plumbing, roof, electrical and major reconstruction

That is not knowing the note business at a level of underwriting risks, assessing collateral, knowing the legal issues of modifications or workouts and securing collateral and understanding the options along the way.An ambulance driver makes money in the health field but they are not a surgeon.

I agree with @Joel Owensso if an investor insists on a lower cut for the sponsor, are they not taking the risk of a less experienced sponsor.Be sure to put a cap on your heart surgeons salary.I personally think that professional athletes are paid too much.

It's a 100 year old home, although city records state a permit was requested for water/sewer line re-construction in 2005.

Teardown - probably 1-1.5 years and then move in.In either case, the place will be vacant until repairs or reconstruction is done.

When a surgeon graduates, he's ready to operate no?

Re establishing a paper trail, I think we probably could reconstruct it as we personally know nearly all the workmen who did the work.