But in terms of cash flow I like this more than an EV charger or renovation.

I understand that reading is valuable, which is why I'm curious to know which book you would recommend for a beginner like me to start with.I have yet to buy my first property but my goal is to house hack every year,  while buying and renting properties to hold long-term until my portfolio brings more cashflow than my W-2 job.

I’m wanting to know there are specific things I should add into the contract before beginning the work, ie: terms, payments, timeline, etc.

Of course, deal terms can vary.  

So now we're rushing into an idea that we've had for a while: Short-term rentals.

I am looking for peace and tranquility in terms of property management.

If you do not understand how NOI and cap rate determine value, learn it even if in theory it only applies to commercial RE.If you flip, you realize the gain in the short term.  

Historically, residential US mortgage rates are near their long term averages.

In terms of a tenant that has paid before and had a lease, who refuses to now pay or no longer has a written lease - this is still a matter for housing court as they are a holdover tenant, not a squatter. 

This is very inefficient especially in terms of rocking, mudding, taping, and painting.