I am hoping someone has some advice as to a situation I might be able to pitch to the investor in which this would be worthwhile for both of us.

Nobody works for free, and if they do....perhaps another look is worthwhile as to why.Definitely good on you for doing the due diligence.

There is such a huge demand for contractors that it has to be worthwhile to find a way to break into that profession. 

They have funky rules sometimes so it's worthwhile to informally check with someone at the VA or a knowledgeable mortgage broker to make sure there won't be a snag.

It is definitely a worthwhile pursuit but you have to remember you are running a mini-hotel service and is definitely more management intensive.

Definitely worthwhile to have a mortgage lender run this scenario for you to see if you'd qualify.

It might be worthwhile asking an appraiser what work might get it marked as resolved in a bank appraisal so that it can market to the mortgage-borrowing segment of buyers at closer to full value.

If your rate is say at or above 3.5%, then it may be worthwhile to at least look into a refi and see how low you can get your rate/monthly payment and what the cost would be. i'd say it's only going to be worthwhile to do this if you plan to retain the home for longer than just a couple years.

You'll have to budget extra capital for the work but some deals in A- and B-class areas (crime safe and good school districts) will have high enough ARVs to make it worthwhile.

Even though zoning regulations are minimal, it's still worthwhile to double check that as part of your due diligence.