The question is mostly a personal financial planning question and it depends on your preference and what balance of risk and access you'd like and would be comfortable with.

Suggesting to them buying their house for a wholesale range offer or lower dependent on the extent of the rehab, then having a contract in place that gives them a percentage of the profit to help get them back on their feet, paying off debts etc.

- Does this answer change/depend based on my current tenant's wishes? 

Selling for $380k means an $80k taxable gain at long-term capital gains rates (0%, 15%, or 20%, depending on income).The $80k HELOC used for personal debts doesn’t affect your taxes.A 1031 exchange could defer taxes, but you’d need to reinvest in another investment property, not a home for your mom.

Hey @Logan Barwick, I personally like option 1, but this depends on what your strategy is to grow your real estate portfolio.

The increased cash flow would make such a substantial difference in your daily life that not paying it off would be foolish.Outside of that, I can't see many reasons I would take a 15% tax hit to save 4% on a mortgage, which is really only effectively about 3-3.5% depending on your tax bracket.

It depends on management style I guess.

Success still depends on your effort, discipline, and ability to execute.

rates are going to be 10 to 15% with points of 2 to 10 points depending.. then you have to have the money for the infrastructure .. 

We are a bit flexible on the budget, depending on cash flow/appreciation.