For the Average buyer this would have been disaster.. we simply built a new construction on it and did OK.. but this full blown rehab can be a real challenge for many .. its one thing to replace kitchen baths paint carpet roof.but when it comes to structural or these really old houses you get from Charleston north into New England.. etc its far more complicated and risky.

Not that the other strategies don't, but yours seems like a logical solution to a number of challenges, for all parties involved in the transaction. 

I was going to challenge you to some BFM like I did @gregory Schwartz.

I like the challenges and intellectual stimulation that comes with this type of job (I work in research and development).

I'm in NY and insurance companies licensed to operate in NY may not be licensed where you are.Also, I own rentals and engaged in several other businesses, and it's best to know and use an experienced insurance broker in your area, preferably a local one.I once bought a business for someone who had his business in an S Corp., didn't realized when his business get sued, lawyers normally sue the entity and the owner personally as well.

I am looking to invest in an rural area that is economically challenged but has a strong rental market in Indiana.

There are a number of purchase/sale/holding costs to look out for, that I compiled into this post here: https://www.biggerpockets.com/blogs/8814/70530-fix-and-flip-project-costs-purchase-sale-and-holdingI see that you're located in South Dakota, so in addition to those costs you'll also need to contend with the Contractor's Excise Tax, which is a 2% tax imposed on "prime" contractors engaged in "realty improvement projects" in South Dakota.

I would challenge you to empower and teach yourself

Cash flow is good but tenants are a challenge from what I hear.

I look forward to engaging with you and others in the forums.