Please feel free to reach out with stories, advice, or any tips in general, and I'm definitely open to meeting people as I begin to get into the world of rental properties.  

We've been around 6-7 years from the last trough in 2009-10 and we are definitely closer to the peak of the wave than trough for the cycle.

I'll definitely be reviewing this often to make sure I cultivate a good relationship with my GC.

Thanks @marknolan I will definitely check out the podcasts. 

It's definitely not the first tenant for this property, so I was on the right path with being able to add these to my "write-off" list. 

Noah,I can definitely assist with your needs in the Milwaukee market.

Yes, I'll definitely be trying to get to some of the meetups this month. 

I know it depends on the context, but are there are better paths i can take in general before trying to secure financing for the house.

There are a great many paths that you can follow. 

That would definitely propel you forward and given that you are a contractor you should be able to come in well under $100k rehab since you can probably do most of work yourself and save a ton of money.