But if the borrower pays off the $120 (likely less since payments being made for a few years reduce the UPB), it's still greater than the initial $60k so do you consider that like a sale and just caulk it up to capital gain?

Do not stress!

Explain that to make improvements to the property requires a little increase and take into consideration their income, time in residence, and try to make improvements that can reduce the overhead.

Im over here stressing $150k-$180k per door.

Tax laws get more progressive over time and in 50 years, you will likely be taxed for even holding equity.You can definitely use some strategies to reduce taxes.

I see that the "Housing Opportunity Through Modernization Act of 2016" changed the FHA rules regarding condo financing and reduced the owner-occupied threshold from 50% to 35%.

What getting them reappraised will do is allow you to take off more debt (thus likely increasing interest expense) and reducing the income from the property. 

Although starting at a younger age, I see no better time then than the present to learn and gain leverage into my first deal.My drive to getting into real-estate investing is to focus on my family of the future, create time to travel and to avoid wasted time and stress thinking about how many hours I may need to work before successfully retiring.

It's almost always less expensive in the long run and usually much less stressful. 

All of those things can move you towards your goals, while being a little more stress free.