I would say, "Deals like this go fine all the time... until they don't!"

It just takes time for most investors to become “rich” off real estate.

Documents off Google never work, as I tried...too many times.

You might want to get in touch with @Andrew Freed and Jonathan Bombaci, they are locked into several of the MA meetups which are great ways to connect with other investors in real life.

As you mentioned intentional flips are typically considered inventory-This means the income is ordinary income and as such: - Is not a capital gain, so hold time of 1 year does not change to a better long-term capital gain rate - Can not be invested in a QOF Deductions related to it can't be pushed or changed- all costs are accounted for with the inventory component 

You may want to make an introduction between your CPA to those 2 colleagues.The CPA can go over their services and pricing to your colleagues.I partner with many people on real estate deals - It never gets to a discussion on whether they do their own tax return or hire a professional.If a partner mentions he will provide capital - does he provide the capital on a timely manner.If a partner mentions he will find deals - does he find many deals and provide an analysisIf a partner mentions he will manage a property - does he manage the property well(find tenants, collect rent, communicate with contractors, etc)

But do you think that 4-5 years is not a window enough of time for them to recover? 

Figured there would be a few data points left out of the equation' that I would need to circle back with :) .There are additional units not rented at this time which could be rented to increase the income.

Make no mistake it isn’t quick or especially comfortable but it can definitely be profitable.As for the rent a room thing in most locales I have to wonder if the additional rent is worth the hassles of dealing with the increased time and liability of multiple tenants in one property but that’s a totally different conversation. 

All things considered, on the market for months, its now winter time, cold weather, holidays, and dark at 5 pm, not prime selling time, I offered $250,000.