Food, water, shelter, these are the fundamental human needs, and when in any form of threat anxiety runs.

The tenant will know the downside so no need to share that but there is a risk that a quality candidate might bolt if this is viewed as an unearned punitive gesture or threat.  

He developed an online course through Eric Thomas and Associates (who I am big fan of).

Attend your local real estate investing associations, get a mentor, feed yourself uplifting and inspiring content (i.e. read some of the books here, read management/entrepreneurial ones.  

@Troy Fisher  I forget about my vendors and other business associates.  

The threat will be if they cashflow enough to handle the debt.  

You'll still have costs associated with the closing and title transfer which you'll likely have to pay....unless your conworker REALLY likes you, haha.

This way she gets a break from other expenses that are associated with running her own apartment that she currently has and also helps you offset the cost on your expenses.

I’ve thought a lot about both approaches but the property I am thinking of fixing up is in the family and is technically not mine yet and aside from needing upgrades it has other problems associated with it.I am currently living in the property I've made some upgrades to the kitchen, bathroom, exterior and interior paint and I’m paying $500 rent that goes towards taxes.

Someone could google the address of the trust and may find you associated with that address.