This is an important distinction because it allows you to maximize your tax benefits across your portfolio. 

I'm curious where the line is drawn b/c I can write off a meal when I am leaving my 9-5 job and going straight to a volleyball match to officiate (second job). 

Probably because the sellers representation doesn’t match reality.

Many hosts struggle at the beginning because their listings don’t match the local market, so taking the time to get this right before launching is crucial!

If the numbers don't match what you think you would like to make on a property, then either you need to discount the asking price to get there or pass on the property.My second thought is what you're feeling and others have highlighted - no everyone is in the business to make it fair for both sides.

There are so many different businesses that can be created around real estate investing if you dial in your personal skill set and figure out the strategy that matches.

My thought with the bottom section was to try and match the style of my original handwritten note.

You will always want to have general liability and property insurance  coverage match the the deed holder.

You can set up templates to save time and customize them to match your brand.

My company also provides insurance, 401(k) matching up to 4%, 2 weeks PTO that can be used immediately, profit sharing ($1200/year), and weekly bonus/commission opportunities.