My fear is at 550K you loose it. 

For example, If you are a landlord with comprehensive insurance where your biggest uninsured risk is tenant security deposit claims, a complicated entity setup is hardly warranted.Whether you have a complicated entity structure or not, you still need to hire and pay for a lawyer if a frivolous suit is filed, unless you are going to allow the claimant to take a default against you or your entity.Be very careful of those who use fear of lawsuits to sell you complicated (and costly to maintain) entity setups.

My fear is that if I don't have a system now in place for managing cash flow eventually I will make a much bigger mistake. 

Back story on the tenants-Both families are super covid fearful and not allowing anyone inside the property at all.

Accessing the equity in the property will take more time and money than the HELOC will because its readily accessible when you need it but I also understand the appeal of being able to confidently know/budget the monthly expenses without fear of a variable rate.

Be prepared for about 50:50 on the answer you get....50% will be in the " a good tenant is priceless and don't risk a turn over"50% will be " you need to keep up with the market rent to maximize your investment, don't be scared of raising rent"The real issue becomes when you don't do it for years and years out of fear and then you realize how far behind you are from market and then you start thinking of big % increases.

My parents definitely weren’t around investors, they both had rough upbringings and have done very well with the hand they were dealt, fear is the biggest thing. 

With the Owner occupancy required with a JADU I fear your return could be dismal.  

I was wondering how many investors here have tenants they fear they will need to evict due to the moratorium being lifted? 

I understand about the insurance and liability but it is a sad state of affairs that kids can't have a swing set because of the fear of a lawsuit.