@Matt Geerts
Hey Matt! Thanks for bringing me back to this post. I do have several updates, so here goes:
Regarding the house hack...my wife still isn't comfortable with the idea, even though now is probably the best time to sell due to property values continuing to increase, and at an all-time high since we have owned the property. Although I have not entirely abandoned the idea, we have agreed to take a different approach to reaching our REI goals. Compromise is the best solution.
Last October we purchased a duplex we found in July after analyzing the heck out of it. A big shout out to the Bigger Pockets team for creating the calculators! Although there are a significant number of duplex rentals in our town, this one was unique. It is located conveniently close to grocery stores, major interstates and the downtown area; much closer than most. It has attached garages and separate laundry rooms for each side. Given the location, the curb appeal and the amenities, we have had no real difficulty in renting it out. We finished rehab on one unit in November and rented it out immediately. The other unit was finished in early January and rented in February. The property cash flows nicely and although it won't cover our mortgage, it certainly covers a good portion. This makes the house hack dilemma much less of a dilemma!
Our next move appears to be purchasing a quad with a partner. We are still evaluating the partnership and we have many details to work out, but it looks promising.