Ideally, we want the entire process to be managed locally to Hawaii to maintain authenticity and manage logistics effectively (stamps from Hawaii and not the mainland).Unfortunately, I haven't found a local company on the Big Island that offers these services.

If you would have worded in rent would that have made her and her living conditions your responsibility to maintain at her benefit?

While still maintaining the tax deferral of the 1031.And when you use that leverage in your purchases of DSTs you also dramatically ramp up your actual real returns on the investment. 

If the Smokies market maintains $400 or more per sqft I'll have about $250k in equity at closing (conservatively speaking). 

If you find a good manager, you can still make as much money (or more) because they will attract better tenants at higher prices, reduce turnover, maintain the property better, reduce losses from amateurish mistakes, etc.3.

Being a builder, my first thought goes to the construction type items: Tile or wood floors, vinyl shower kits, high quality wall paint like Behr Marquis, solid wood furniture, good appliances not cheap rental ones, easy to maintain yard outside like DG, artificial turf and gravel. 

They seem to require high quality materials and  craftsmanship to maintain a level surface.

Setting up and maintaining an LLC comes with annual administrative costs, so another thing to consider is your cash flow.

I've run STR/MTR/LTRs and it will be very difficult for you to maintain a solid calendar with only MTRs.But definitely fine-tune your dealings with ABNB....they will ruin you.... 

The nice thing about this strategy is you maintain the cash. flowing asset in Chicago along with the appreciation, even if it is low2.