I personally would stay away from condo-tels as they will be even worse and you'll have less opportunity to cash flow. 

I personally don't mind cooking on electric but I will say that cooking on propane is different than what most people know which is natural gas.

Your first step is- Get approved for a loan (unless you plan on paying cash). 

If you have bank loan (not an agency loan) or no mortgage at all, an LLC is certainly an option.

I've been self-employed for only 6 months, and loans are proving difficult to come by despite my great credit (not to brag, I'm moreso frustrated and seeking help).

I'm not sure I can copy and paste my Excel spreadsheet, so i will approximate the numbers here.Strategy:Take a Home Equity Loan (second) on our primary @ 5%.Pay off existing HELOC (variable, at 7.5% now), use remainder ($120k) to buy the land (plus 30k of our own cash).

I tried to create rapport with the owner over the phone but waited to present my real agenda only in person.   

10 year (the common benchmark for CRE loans) just keeps climbing.

Your loan would be on a different property so no financing on the property you are buying. 

Some of the heavy hitters here in Chicago discussed the ADU program with a very nice person from the building department.