I wouldn't lose any sleep over people trying to force him to sell.

You can have a 2% property that still loses money.

I could save about 300 dollars a month doing it on my home but do not know if I want to risk losing my home to invest in more properties.

This isn’t a rate of return question it’s a “how likely is it I will lose money”QuestionThank him for being so thoughtful about it, offer to keep him posted on the progress and pay for lunch.

Its the best way to lose both.Using for your own investments probably makes sense, although I'm not sure how it would do that. 

Walk away and lose my earnest or buy it anyway?

The final escalation amount should be a "I don't want to lose it over this amount" not a large range to cover huge swing in price.

I have not purchased a home yet. My goal is to purchase my first multi-family property this year. Question- If I purchase an investment property (where 20% down is required, so first-time doesn’t help) will I then be ...

I am losing my mind trying to figure out what to do.On top of the general change in career I am struggling to decide whether or not I would prefer to do commercial or residential.

To use your own phrasing, I think your true "stupid tax" here is losing a formerly reliable tenant because you have to evict at this point.