My goals are to provide financial freedom for my future family and establish a sustainable safety net if physical limitations prevent me from retiring from my current W-2s.

Unrelated to HOA but if homes won't pass the safety engineered designation, who demo's house and haul off and when does HOA or city make owner to remove?

They bring food and hats and other marketing materials.

Maybe as an additional safety net set your DSCR% or cash on cash return a little higher than other areas you own. 

If oven, washer, dryer go out, I would pay them some money for during the week for food to eat out or laundromat, and then fix on the weekend.As you said you're in the learning phase.

You have to confirm there are no pending assessments and lawsuits against the HOA before buying and an assessment usually comes for roads, roofs, windows, decks, and stairs that were not done properly or have a safety issue.

This should include which areas you can access, what hours you can work, and any safety measures you’ll take.

Looking to purchase one and struggling with the right calculators to determine the real metrics.As I understand it (recently looked at buying a former bnb) you need to treat it like any other STR with your extra costs such as food, etc  baked in to the expenses.

Have your agent throw a broker open (possibly with food) to get agents through and get feedback. 

This included installing new tile flooring at the front of the house to enhance curb appeal, upgrading the electrical panels for safety and efficiency, and putting on a new roof to ensure long-term durability.