It depends where you are on your wealth and life ladder.

With record low inventory and sales transactions there's no low hanging fruit.In this market we think the best opportunities are value-add (BRRRR'ish), zoning changes allowing density (ADUs), or seller financing deals (buy a lower rate).

I gave him some ideas of what he could do depending on if he wanted to be more passive or more active.

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.

Assessments are dependent on what they were for.

It will also depend on your goals.

I have some experience here, and my answer will be it depends. 

The management companies & local investors usually lease places up within 1-2 weeks max (depending on if you want to hold out of higher rents) How would you think about leasing these out? 

Also, you will have additional occupancy tax depending whether you are in the city limits or not.

If so what are the interest rates on those debts?