In the event of an emergency, I can borrow from the HELOC, a loan on MY investment property, up to $50k.

I would consider investing with you, but I'm not ready to commit my "emergency" funds for four years.I am actually 4K to 5K short a month for retirement.

Call the non-emergency number for the local police station and ask them who to contact to get information. 

This is the program: About Good Neighbor Next DoorLaw enforcement officers, pre-Kindergarten through 12th grade teachers, firefighters and emergency medical technicians can contribute to community revitalization while becoming homeowners through HUD's Good Neighbor Next Door Sales Program.

Will I emerge victorious from this real estate labyrinth, or will I be forever lost in the sea of "what ifs"?

It’s good to have some savings for emergencies, and you should look into different chances to grow your money.

Handling Maintenance requests and emergencies, Handling tenant disputes, Ensuring the tenants are properly insured (if you require them to), Marketing the property, Screening applicants, Handling the security deposit return, and a whole lot more. 

I've also learned not to respond to tenant's calls and texts immediately--especially if it's in the evening--unless it's a true emergency.

Alternatively, if something were to arise in our life (emergency or otherwise) while this money was tied up in an investment, we're left with few good options. 2) Time is not something I have much of.

Also, as another member pointed out, always put a maintenance spending limit per month per property in writing Anything above that should require owner approval before proceeding, unless it is an emergency type of repair such as repairing a burst pipe indoors or removing a fallen tree limb from an upstairs window.