Is it worth spending the extra $24k to you to keep these in your portfolio for 5 years?

My plan is to 1031 this into a duplex.

(I’m working on getting the wife onboard with our long term plan, too.

In both cases I spend a lot of money rehabbing a house and then pay myself back either through a sale or refinance of the property.Up to this point, I have primarily just paid for everything through my business checking account.

You get grandfathered into the codes that were in place at the time, you get the old setbacks, you don't pay an architect, engineer, city and permit fees, plan check costs, school fees and other costs that will not come with an existing house.Not saying that you can't build new for less than a remodel, but not usually when you add in all the costs above. 

I am based out of Janesville, but spend quite a bit of time in Madison as well.

I'm planning to use VAs to help with the first part that you mentioned - qualifying homeowners based on interest in / willingness to sell.

I use a lot of different cards based on the best categories on my spending for cash back/miles, but one under the radar for rental investors that gives 5% cash back on up to $2,000 spending per quarter on utilities category when chosen is the US bank cash+ card.I max out on utilities spending with the card every quarter.

Looks like one is better for a flip and the other has an incredible upside with equity so we plan on holding that one. 

If you can't narrow it down significantly you'll likely get overwhelmed and spend a lot of time going nowhere.