Seems like a win win to me.If I went into another market first, I feel like it would be doable but a slightly more uphill battle.

About the 16k, if you do the work yourself it might be doable but it will look like a 124,000 dollar house because you would need to be cheap on material. 16k comes out 12 dollars a square foot which is low.

But, having said that, at least during a decline it would seem to be fairly doable to see values consistently dropping with each passing month to recognize that the market is in decline.

I say yes but it’ll be a C class property, if you’re okay with that, then it’s doable.

Is it doable, yesShould you, maybeBest of luck

Its definitely doable.   

Honestly, I've never actually seen what I proposed done, but I think it should be doable in a lot of original build-out cases (as long as there aren't local or state laws that don't allow a separate "class" of units within the same HOA). 

It's totally doable if you get the right teams in place.If you move, where would you think you'd want to go?

My end goal is I want to retire from a normal 9 to 5 job by 40yo, which is 10 years away and I feel its absolutely doable.

It's doable but you will need to make sure you have the reserves for repairs like that.