I will not be using an LLC and so will pay landlord insurance and be able to make deductions directly from my personal income.

You can do some sourcing yourself through Facebook groups, and online RE communities , and even pick up the phone and cold call some homeowners that may be tired landlords, don't owe anything, and have built up some equity.With enough volume, you should come across some solid deals.  

Wisconsin is not a landlord friendly state by no means, and after 7 years of being a landlord I am just now finding this out.  

Some folks have gotten used to low quality landlords that don't fix things and think that is normal.  

Examples of pitfalls include purchasing in an undesirable area, not understanding the market values (vs. list prices), not knowing the rental values (current and market), inheriting bad tenants, buying a lemon, going rogue on renting and management with no contacts / systems / no legal understanding of PA and Municipal landlord-tenant laws, not having trusted resources and contractors in place, using out of state lenders or shaky financing, throwing lipstick on a pig when renovating a house and wondering why it's ARV isn't increasing, tenants are renting, etc.

So have some lite experience being landlords but are very interesting in real estate investing by way of flips.

Is there a Landlord application to fill out?

If things go sideways and the landlord/owner must evict the tenant/purchaser, a court could force you to eject the tenant. 

Class A Properties/Tenants: just need basic understanding to start and can learn as you go along.Class B Properties/Tenants: a decent amount harder, you'll need to invest a decent amount of time learning landlording or tenants will teach you a lesson.Class C Properties/Tenants: you need to really know what you're doing and have boots on the ground you can trust.Class D Properties/Tenants: don't even try!

We became "accidental landlords"...it just happened.