Actually a lot of the info you'd get from an operating statement (gross rent, expenses, NOI, etc.) is available on many listing websites like Redfin and realtor.com, albeit not as up to date as the MLS and not always accurate but that goes for all data provided by listings.Regarding MLS access: it is protected carefully with various methods such as keystroke tracking, IP address, simultaneous login etc. and agents can get in a lot of trouble for sharing their login info, which is good because within the massive database is a lot of private info that can be dangerous in the wrong hands like lockbox and security system codes.

I have a contractor who reached out to me and wants to partner with me. he wants me to secure the property and pay for the material and the work but wouldn’t that just be me hiring somebody?

If your after long term investments then there are other more secure ways of making a 7 to 10%+ on your money for example like buying A paper notes ( mortgage Notes) than a saving account or stock market.

How much do you ask for when asking for a security deposit?

Better for taxes, more secure and you have a bit more of control.

By paying it off you increase your security. 

The window concern almost broke by heart, as the winters here in Wisconsin got to -38F this past winter.

I could move into a property that looks like a good deal (either in SF or the Easy Bay) and secure an FHA for 3.5% down by virtue of living in the property as my primary, rent out additional rooms, and essentially function as the property manager.

Conrad, look up Brew City REI Club if you are interested in participating--it is a private, give and take, invitation only real estate club of active local investors obsessed with real estate in Wisconsin and charitable in helping each other succeed.  

I'm looking for someone in the Fox Valley, WI area to learn from.