I have to frequently temper my outlook because a carpenter / builder thinks one way while an investor has to tone down the "quality" a bit.... 

Buying refurbished washer dryer versus new does come with the potential for more frequent breakdowns.  

You have to know your audience and what type of investor you are approaching.

What frequently happens is that the overhead for these 'businesses' take too much of the cash flow and people try to circumvent by renting single family in areas that they think will help them with some sort of invisibility, no local taxes, zoning inspections etc. ie: grifters.

I'd like to stay away from long distance investing for my first investment because I expect things to go wrong and I'd like to be able to visit the property frequently if needed.

As a broker consider a similar move the things I have realized in RE is that people are so hung up with the social side to real estate that they frequently make decisions that are harmful to them.  

How frequently can I switch houses when I house hack?

Any money you take out as debt is not tax free even if you put it in your pocket. ( all though I recommend you invest most of it. ) the rich frequently pay them selves with "good debt" and why wouldn't you its tax free.

@Yosef LeeYou don’t have to wait, but be honest with your audience on where you are with your journey.

Definitely avoid anything that would require frequent maintenance or re-planting.All in all I think you have a sound plan.