I lived there for a couple years and I met this guy who has bought and managed a ton of property there. 

Based off of the podcasts I am listening to and other property management professionals that I network with, that has been the experience of portfolios across the states. 

If you have one high earner as a W-2 I would recommend the other switch to managing the Real Estate side of your wealth ASAP. 

Look to learn, and hopefully implement converting my duplex into an assisted living center. Any advice or direction on how to go about this in Wisconsin would be greatly appreciated.

Looks like I need to talk to my accountant, but I was hoping to have this squared away before talking to him.I realize I also have this problem with my property manager.

That's up to my operatione manager.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Do you work with a property manager or do you do everything yourself?

Basically, the further you get away from the city the more potential for cashflow, but you're also dealing with a different tenant base that may be tougher to manage.

Newer buildings now have state-of-the-art amenity packages with pools, gyms, co-working spaces, high-speed internet, and community gathering spaces where savvy property management groups will have apartment building events to encourage this sense of community, all being a level of convenience and neighborhood community people cannot get anywhere else.