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.

They can now make the best decision for them on a management company to hire. 

I know the decision shouldn't be made of tax benefit alone but starting to think other areas may help me accomplish both more efficiently.

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?

It might be a better decision to do a 75% Cashout Refinance.

This can put a significant strain on your finances and cash flowThey also often require a large down payment themselves and may have a strict repayment schedule that can be difficult to meet, especially if there are unforeseen circumstances or delays in renting the property or generating income from itIn addition, relying on this type of loan may expose you to higher financial stress and the possibility of default if you are unable to meet your loan obligationsThe final decision depends on your overall financial situation, risk tolerance, and your ability to manage the associated costs and obligations

Then make the decision if being a hands on landlord is something you are realistically interested in. 

This is the emotional journey I went through and the key business decisions I made along the way.

While this insight is valuable, it’s important to remember that thorough analysis is always crucial before making any final decisions. 

Could be a business decision based on keeping long-term high quality tenants rather than risk the costs on turnover.