We live on a small farm and I built the basement out with rustic accents which make it kind of appealing (i think).

I'd tell them to invest it for themselves in an index fund if there wasn't any appealing buy and hold properties you had your eye on.I would not force buying a property just because the money is available.

One thing that was appealing to me was that there was a section 8 tenant in there and the rent was high enough to cover the mortgage and HOAs and then some.

I've decided to look outside of the area and found the Central Valley to be most appealing due to job creation.  

(renters is key word, I think there's more of an appeal for homeowners and those with families - I'm making an assumption that the majority of families in southern NH with an adult commuting into Boston are buying and not renting, but please correct me if I'm wrong)  To me I think the draw to southern NH needs to come from growth in southern NH (such as the tech you've mentioned), or growth north of route 3/95. 

One major appeal is that real estate is a tangible asset that you can physically control as opposed to the the stock market where we have 0% influence on our investments.

I have to agree filling it in would solve your repair concern and appeal to more potential buyers..

Some of the Midwest deals I'm seeing look very appealing compared to prices around my area.

*Number 1 seems more appealing to me, as I'll be the private landlord (and can save on costs there), and I know those cities so I feel comfortable choosing the right property.

If someone tries to sell, many of these properties only appeal to investors.