I need some practice with something "easier" before I go full bore.If you've read "The richest man in Babylon", it says that a good investment is one where your principal is safe. 

Getting it zoned as a tri might work, but I’d play it safe and run numbers as a duplex.

While some contractors work on a 1099 basis, I worked as a W-2 for safe harbor reasons (the IRS has vague rules about who is a contractor and who is an employee -- picking the wrong one can get expensive for the parties involved when the IRS disagrees with your choice).I also had to learn how to live on a lumpy income stream as a contractor (if the agency didn't have a project for me to work on [no "billable hours"], I didn't get a paycheck).

I’d like to get her a safe place to live but can’t afford to cover the difference if she can’t pay market rent, so this seems like an ideal solution to keep her housed and safe.

It's not just personal credit at jeopardy here, an owner is responsible for providing a safe and healthy living space which means fixing things which means additional capital.

But not sure if i can fill the potential of the land, because that's what your paying for in this property in the super safe suburban area right off the highway, not the tiny house on it.

@Joe Engelhardt You can use your HELOC as a downpayment, season your mortgage (6-12 months, to be safe) and see if you can re-finance into a conventional mortgage.

I would probably estimate vacancy at 8-10% to be safe as well as raising your CAPX and repairs to 7%. 

Is the person who has never invested in investment real estate but just sold their primary house or farm or small business better equipped than me to analyze if a syndication deal on a 50 unit apartment deal is 'safe' or not?

Denver is a reasonably safe city compared to many and our public transit is finally catching up, albeit slowly.