My wife and I own a two-flat in Chicago, and we're planning to upgrade our heating system.

They are purely for investment purpose and will require you to sign a non-owner occupancy affidavit at closing stating you don't plan to occupy the property for more than 14 days out of the year.A second home loan is as it sounds, a loan for a property that you will use as a second home, and live in.

Well, unfortunately I'm quite sure I didn't yet understand where you're going with this, but... they are the basis of how I can achieve net yearly ROI of ~8%.

Be confident the mortgage company, and the wholesaler is well aware of the procedures and will out maneuver you, even if you are factually correct. 

I plan to manage it myself.

Maybe women as a whole arent interested in these jobs or flipping houses > On my jobs the the women work as designers for the hard surface company.. we have a few women I see working for the sheet rock company doing the fine detial mudding and patch work and well when I was in the logging business one of my loggers his sister ran the log loader and was very good swinging those logs on to the truck..

Over the next year or so, I plan to learn as much as possible while also connecting with people in my area to gain a better understanding of the market and opportunities.

Social media can be a powerful tool, and then good old-fashioned door knocking for listings is a great way to drum up business as well! 

Is there a program or software that allows you to easily observe all the properties in your portfolio, as well as their details?

I'm just really frugal and really efficient in the way I plan, shop, and execute.