Ideal time to start, build a database so when Spring time comes you'll have business.

I don't necessarily mind not cash flowing but obviously not ideal situation.

I was first searching for small multifam properties, but have been getting more settled with the idea of a 3bd single family home with a basement that I can convert into another bedroom/studio (I'm a musician/drummer, so it would ideal to have an area I can work out of where I also live).

You should have a trusting relationship with your realtor who ideally has investment properties in the same area and they should be steering you clear of a poor purchasing decision based on area and condition.

They want a comfortable desk and office chair and, ideally, they want it in a room they can close off from the rest of the house for quiet and privacy while in meetings.

Personally, I like the idea of house hacking, ideally once per year, or as frequently as you're able to qualify for the next house hack.

I assume that the majority of tenants would likely be travel nurses so it seems logical that a market with a large hospital would be ideal...I just feel like there are a lot of cities that have decent sized hospitals so I'd love to hear opinions on what markets could be most profitable. 

The ideal situation would be to own the property.

Medical Payments (covers medical costs of an accident on the property)There are many endorsements available and you should discuss the coverage with a qualified Independent Agent (they represent multiple companies).An Umbrella policy provides an Liability Limit that can provide coverage if a claim exhausts the limits of your Homeowners, Auto, Boat, motorcycle, etc. policies.   

I'm trying to get some cash flow from my first property, ideally, at least $200-$300.