I will be able to travel on weekends to visit the property and oversee progress to a degree.Is this something that people are doing? 

They will be able to do much more than a generic evaluation when they evaluate your loan andyour specific property.

I drove passed the house frequently and was always excited to see the progress.

Any specific advise on how to find, evaluate, negotiate, and select a landlord insurance policy would be greatly appreciated!

Things to consider:-I need to be in a city, walking distance to a business district of some kind-I'd like to follow a path of progress within a city, and don't mind being close to (but not within) sketchier areas-a market where the average 3 bed 2 bath sells for under *ideally* 250k, but up to 350k (I'll be looking for a property that needs work, but this sort of market)-must be SF no association-I'm 31, single/no kids.

Might want to evaluate who you work with. 

What do you guys read, sources, websites to evaluate and assess the housing market at a macro level and regional level?

Here are a couple reasons why... you don't have to spend advertising dollars and spend massive amounts of time learning how to become an expert advertiser while at the same time trying to learn Real Estate...It  allows you to focus on developing your acquisition skills, negotiating, evaluating, at scale and at little to no cost.

@Vann Calhoune As a Florida real estate attorney myself, I prefer to work with documents I have prepared in the past rather than evaluating something I have never seen before and modifying with language I want to include from my form anyway.

You would need to provide more info on the property to be able to evaluate whether or not it is a good deal.