Are there property management companies out there that also offers bookkeeping services to the landlords?

YET, I managed to have my rent paid ON TIME every month, even though I hardly occupied the house.

(Approach - 2) - He says that if he is asked to pull permits, he is not responsible for any additional work that the inspector may throw (basically more money out of my pocket on the rehab costs).

The BRRRR combines all the things that can go wrong with rehab and managing contractors with the holding costs during the time when the rental is being seasoned, and then you are literally at the mercy of lenders who may or may not refinance you at a rate that will allow you to cash flow.

Is it easier now than ever to manage a short-term rental?

Finding a solid property management team is crucial, especially when managing from out of state.Having everything you need under one roof can really make a difference.

We have a few projects under our belt that we also own/manage at this point...we completed an 8 unit project (all rented) and we completed a 5 unit project (all rented) and we are in-process on a 9-unit project and have a larger one in the hopper (maybe 18 small units that will be sold, currently has two units rented). 

I would make a list of all the work, and for the appraiser include the costs, so they can justify the new valuation. 

Have you talked to contractors about the cost to build? 

Of course the bolder the target, the less likely it is and probably less than .01% of people could pull this off.More realistic advice is to get as high of paying W-2 job as you can, save up, put 5% down on a 2-4 unit, manage the heck out of it, and then leverage that experience to do a larger deal using OPM.