With all this talk about 1031 and individual situation(s) being the key component....Since this is a common analysis, there must be a comprehensive analysis tool already in existence. 

If they can't figure out their issues, don't renew and find new renters.If one of them wants to rent alone, check their financials to confirm they can afford the rent alone.

House hacking is a great start, but it is important to keep in mind potential downsides like privacy issues and the stress of managing tenants.

Make sure to reach out to one with real estate experience as location is not longer an issue.

When it comes time to negotiate, the buyer will have his/her opinion on the matter so I’ll be somewhat dependent there, but it’s good to know the tax “mechanics” won’t be an issue and have a few reasonable options.Quote from @Michael Plaks: @Matthew HeffernanTax question first, because it's very easy.

To make things even more complicated, I could possibly have roof issues, which means more $$ spent that I won't earn.

That in itself might be an issue too. 

I also would not limit by education although we do see it a little locally where some rentals will not take undergrads only grad students and it doesn't seem to be an issue. 

It is not even an issue of the hours and hours this research takes up.

This is the sledgehammer to be used only if this is a major issue for you and you are willing to take the cash flow and renovation impact now.I would do #1 and #2.