A 3' wide continual walking space perhaps? 

I just feel that I can't pick a winner in this space confidently right now. 

I would base your answer on buying the bigger one (within reason) that will fit in your space that fits your budget.  

Consider creative approaches like short-term rentals, ADUs, or co-living spaces that maximize income in limited spaces.

But they asked for a little space to store their Christmas items. 

We do Urgent cares all over the county and get pitched med office spaces all the time, and none fit our profile for visibility, for our use at least, only because we follow a more "retail" modeled approach to site selection, given the business type.  

fyi, one of my children (also in Indiana) had a very good experience with a VA loan through Veterans United.If you can find a tenant who wants to be rural and have space but doesn't have a down payment or for some other reason doesn't want to buy or can't buy, that person could be an excellent fit for your situation. 

It includes space to spell out specifically what the tenant is responsible for.

I don't know how to get started as my current property manager is not familiar with the mid term rental space so I am looking to self-manage but not sure how.Any advice is much appreciated.

Based on your ideal loan terms, here are some thoughts on the funders you’re considering:RCN Capital: Well-regarded for their flexibility and strong presence in the hard money space.