You won't pay tax on 250K (single) or 500K (married) of the gain. 

As you gain experience the fear will subside.

My two cents, and more importantly to save you time, energy, and capital; I would potentially consider looking into other side hustles to gain additional income.

Investment Info:

Other other investment.

Purchase price: $50,000

Cash invested: $700

Sale price: $99,685

Vacant lot that we flipped for a profit after the first year of ownership.

How...

You may be gaining muscles now, so while your body is getting stronger and healthier, your weight does not go down.

Do I try to learn how to become an Airbnb host + gain STR experience and try to do it in my market?

Our goal is to utilize the appreciation we've gained to re-invest in something more active and produce a higher income. 

With the market, I (like most) have gained a fair bit of equity over the last few years.

It is definitely a team effort once you get started, then as you learn you will gain traction.

Over the past 4 years, I've gained a significant amount of experience including a large respect for how important it is to truly understand your market & have many personal connections with people operating within it (Agents, Wholesalers, Contractors, Subs, PM's etc).