Make sure you can handle the unexpected aspects of doing business as a landlord financially and with good business sense.

Hi Austin,Insurance business is complex, and I wouldn't rely in an agent that is asking you to leave things "as is".In my case, what worked is to build relationship with at least 3 to 4 agents, so I can easily email my portfolio and they quote me based on that.

You can do all at once or chunk it over several years or whatever amounts and timeline makes sense for you. 

Which in turn will bring plenty of other investors and general business to the market.

I was out of town at a conference when an old business partner "went hard" with $10K on a property.

In NYC starting a midterm rental business.

Personally, we are diving deep into buying and operating businesses that potential to conservatively achieve 20%+ cash on cash returns.

My wife is a veteran real estate agent in SF and is very focused on continuing to build her book of business, so I'm leading the charge in the household on the investment side.

I think it also makes a lot of sense in many ways to invest in what you know....and that's often closest to home, but not always.Also is Milwaukee known to be landlord friendly or landlord adverse?   

I am hoping someone educated can chime in on my specific situation.I am a high income earner, owning a construction business that specializes in wineries and luxury residential.