I think you would need to ultimately know what your goals are and honestly what your budget is.

Set a goal and then connect the dots by taking action each day to reach them.

Your goal of buy and hold and flipping so soon seems very difficult, especially with a young child (our first is due in January).  

Our goal is to design/build a house that can legitimately be a big SFR or a Padsplit property.

So I’m trying to see if I take that equity off the table and re-invest the sale proceeds in another market across more doors where we’ll see better appreciation, OR if we continue keeping it as a rental and work on principal pay down even though the rental price has been coming down and the home is not the easiest to fill because of the above average price for the C- to B neighborhood.Ultimately, my stated goal has been to build appreciation (over cash flow) by acquiring 1-4 doors per year for the next 10 years to allow my wife to retire (or be work optional) by the time she's 50.

Both can align with your goals—just weigh the cash flow vs. upfront cost trade-off!

Our goal is to create a dynamic that both parties can benefit from and be happy.

I’d say investors that choose better locations and better properties within those locations will have a much better chance of success as the big risks will be minimized (by better properties I mean with less deferred maintenance, not necessarily newer but newer can sometimes reduce operating expenses, or older with “good bones” that are well maintained, especially if you’re needing to outsource any work and manage it remotely).

I'd suggest choosing an area that looks like it has potential and then spend your spare time just driving around.

For anyone in real estate, it’s definitely worth exploring how private money can align with your goals—whether you're borrowing or lending!