A typical policy for short term rentals is going to cover most, if not all, of the perils you have listed.But if it is a homeowner's policy or standard landlord policy, the insurer may well deny claims, since the property is being used differently than what is described in the policy. 

Whether it's good or not is a whole different question.

Partnering with an amazing agent and focusing on flipping/a normal job/different business can be a lot easier than trying to learn the ins and outs of sales as a Realtor.

Also I will be renting out my condo as a mid term rental (to travel nurses) does STR insurance fall in the same category or is that a whole different policy? 

I was very pleasantly surprised.I also built a tool myself, I had a lot of issues finding service person for different repairs need.

Since the property has vacancies, a buyer might discount for lease-up risk, so that’s something to factor in.I owned a multi-use property in IL that is definitely different than what you're looking at.

(a) Is it okay to be looking at 3 different areas VA, MD, WV?

Are saying it's a better idea of figuring out and going after a specific niche or group of people who have a reason to downsize or need a different type of home?

I understand it’s a different market but I think $1200 is a pipe dream.

But you're talking about keeping it yourself, which is a different analysis.