Thus, my main goal joining this forum is to try to gain confidence in the decision to get into real estate investment and better understand the risks that I may not be considering due to my lack of experience in the field.

No one right decision for everyone. 

That being said, that decision has resulted in a portfolio of over $200MM and my life has absolutely been changed.

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

Considering how rising prices might influence people's decisions is interesting.

However if you understand the process already and what you're trying to achieve and just looking for someone to do it for you, then I would search a bit more to price compare and then make your informed decision.

Is this a wise decision to use a HELOC on property number one that only has 20 to 25% equity in it to fund a down payment for a live in house hack in multifamily property number two?

Joining a coaching program is a big decision for any real estate investor.

No decision yet, but it's looking good for the investor, as they were able to find about 20 other houses in the area that have been operated as STRs for years with no complaints.

Quote from @Todd Anderson: @Benjamin Ying,First off Congrats at making the decision to get started into REI and getting involved with BP.