Other advantages of doing this --  vet your local contractors  for future repair work -  interview / pick PM  while still an area . 

If you are just starting out you can walk the property with a contractor for the rest but if you end up not buying the property expect to pay them for their time when you have them do a walk with you unless you never want an estimate again.

Maybe, you could help with insurance for the business, but my guess is that most real estate agents are independent contractors and do not have large businesses.

looking for a contractor who can walk through with me to see what needs work and how much it might cost.

First , the guy you get off craigs list isnt a contractor , the guy swinging the hammer isnt generally the contractor .  

A 203k is what I used on our personal home and let me tell you, it was a MISERABLE experience, but at the time, it was our only option as I had just started a new job and had to do a 90-day "trial" as a contractor.

Our original contractor lost his license due to copyright infringement.

Google what it costs locally for a siding contractor or call around and ask what they charge per square(100sqft)If it’s just a few spots you can still calculate your material costs but it will be tough to get your labor cost without someone to look at it.

Just make sure your contractors are lined up or possibly get more subs to make things go faster? 

I want to learn the whole process from being a landlord to dealing with contractors.