@Aaron Hunt You can insult me all you want, but it doesn't change the actual market data.As I said, there's no guarantee that the trends will continue. 

If you payed a contractor, then you would each be sharing that  20k worth of cost and nothing changes other than everyone makes a little less.   

As an example Philadelphia about 8 years ago changed the law from exempting IRAs, 401ks, HSAs, etc to making it mandatory to pay sales tax and have a business license.  

I think he's done 2 webinars with Brandon and Josh on BP.I would look into changing the utilities you pay into separately metered for the individual apartments and get that off your back and make the tenants responsible. 

It might be able to be done without even losing a bedroom, but even if it goes from 4 bed 2 bath to a unit with 2/1 and a 1/1 unit, the rental income (or sale price) should be higher than a 4/2 SFR in the area.That said I'm not sure if there's something I may be overlooking.It already has 2 exterior doors positioned nicely with separate porches and room to have cars parked on different sides of the house (it's on a street corner).I looked up the zoning regs for how the plot is classified and it is allowed by right (don't need to apply special allowances or rezoning) to have multi-family housing on the plot.The rehab would already have it gutted enough that the changes to plumbing and electrical would be easier.I don't have any idea how hard it is to get separate metering for water/gas/electric. 

Milwaukee County is likely to see change as a result as well as southern and western Waukesha counties.  

How does this change the seasoning requirement from the perspective of a lender? 

I have decent credit but will be changing employers next week.

Interest rates going up and the changes to SALT deductions will make it more costly to own, which in turn will put downward pressure on sales prices.

You may want to sell in 3-5 years because your goals or life has changed.