I would concur that since you would be investing in WI and then living in another state, you should consult an accountant to determine any tax liability you have and where. 

Now we're seeing investors pouring money into buying Class C rentals - but, many are getting burned.In our experience & opinion, the main determinant of property Class is not location or even property condition, those are #2 and #3.

But right now your biggest question will be determining eligibility to purchase the next one. 

Under Oregon law, landlords may not raise rent more than once every 12 months, and the maximum allowable increase is determined by the lesser of 7% plus the annual change in the Consumer Price Index (CPI) or a percentage set by state law.""

The biggest shift is deciding whether you’ll lease by the bed or by the unit, because that determines how the management agreement and leases need to be written.You’ll also want clear rules on guarantors, turnover expectations, and who’s responsible for damages.

Determine your RE strategy and don’t hop around.  

“I don't have the knowledge to walk through a house and determine what rehab costs would be.

The solve/help needed:I am determined to make this work, am super type-a, and want to get this deal going to make a plan to massively scale beyond these 20 doors.

If you are determined to use this 401k to invest, you will rollover this into a self directed IRA with a custodian.

@Kevin CarpenterI typically use Batch Leads to cross reference all the properties currently on the MLS to quickly determine the loan types on listings.