@Deb Bandyopadhyay Welcome and congrats on getting started...if I could say one thing it would be to do your homework, but take action...listen to your agent and your gut and pull the trigger on your first one.

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If the numbers make sense and there is some cashflow, pull the trigger.

Do I wait or pull the trigger and potentially regret later?

I ended up pulling the trigger on this deal, working to get it under contract now.

Would that spread our gains over multiple years, or would the sale trigger the capital gains tax regardless?

Could trigger the due on sale clause but extremely rare.

Been meaning to do so for a while now but can't ever seem to pull the trigger, I believe this is due to my perception that I am not yet educated enough to do so.

At my current phase, I am building my education, building the capital, team, and plan/strategy and looking on pulling the trigger in 2022.I’m in a currently unique position.  

If you had more equity and had to choose between the two the answer is it depends.If your rate is high and you can lock in a much lower rate ( by about 1.5-2% plus ) then the cash out refi is the best choice , also if you already had a property or two you have in mind that your ready to pull the trigger on and put in an offer for.If you are unsure of a property but you want to be able to borrow when the time comes, the HELOC is better because you pay no interest until you withdrawal the funds and you can do it on any given business day.