Sometimes a deal can be slightly negative because you're living there as a house hack now that is a different story because you might "know," that when you move out it will be positive or positive after you raise rents and move out (lets say its a fourplex 4 flat for Chicago folks, and 4plex for us west coasters).In this case, it might be lucrative because in this example you control the "move/out," and conversion from negative cashflow to a positive cashflow scenario so the future potential is definitive versus some hope and prayer that you will someday cashflow (smoking hopeium so to speak).I've also seen some buy negatively cashflow properties here in Seattle PNW (pacific northwest) areas even after they move out (its still negatively cashflowing), but the aim was to build ADU or accessory dewelling units in the back and that eventual exit strategy would yield positive cashflow eventually.

So as an investor here, it doesn’t particularly bother me that Detroit has gone on this roller coaster ride since the other areas are showing very positive signs.Is the recent appreciation data/success above most likely because the market previously dipped 50 years ago and then again in 2008?

From the beginning of the "Fed Rate Roller-coaster" ride started it had been running commentary as to "what will the Fed do", and when I had been asked I replied like a broken record "well, what did they say they would do?". 

Like Taz said, it can be more of a roller coaster LOL.

As I get older my appetite for risk gets less and less and I don’t need roller coaster rides I like the merry go round

Let's break it down in simple terms.Imagine you're at the amusement park, and you have two options: a roller coaster and a merry-go-round.The roller coaster is thrilling and full of ups and downs, just like the growth path in real estate.It can be exciting, but it also requires patience and the ability to handle unexpected twists and turns.The merry-go-round, on the other hand, offers a smooth and predictable ride, much like the cash flow path.

I spent the last 17 years working in the Internet industry, a roller coaster ride of feast and famine, only to land here.

@Brittany Bauhaus Welcome and it's nice to see a fellow Central Coaster! 

Enough information in a timely fashion to keep you updated but also allow the Property Manager to effectively run their business without putting you through an unnecessary emotional roller coaster ride.

That is the roller coaster ride of real estate.