@Shirley Rozenshteyn I understand, it does seem like an upper scale area.

@David Smit"Where imposture, ignorance, and brutal cupidity, are the stock in trade of a small body of men, and one is described by these characteristics, all his fellows will recognise something belonging to themselves, and each will have a misgiving that the portrait is his own."

Areas that are hot include Downtown, Bayview, Brookfield, Wauwatosa, the Lower Eastside to the Upper Eastside as well as north of UWM.

A guy across from me overpaid for a fixer upper ($1.3m). 

Although I am an infant at this game, I have a lot of beliefs and diet tips to maximize your brains potential and your bodies health.1.)

If I can manage to just get a fixer upper property with at least one other unit and a mortgage under 4k then I will be paying less than any of my neighbors, I'm optimistic that with 6 months to hunt around I'll be able to do even better than that.Sorry I don't have any solid numbers for you yet but that's the plan, house hacking seems like a really safe first step into the real estate biz because of how even if you're still left paying a little extra on the mortgage at least that going into a property you own instead of just disappearing.

It’s what makes me feel the problem is the price OR that simply the area is turning into an upper middle class area too fast for the people to keep up.

I'm assuming with you being a realtor for a while and working with investors, you would have the upper hand in getting investment properties right?

There is a reason why corporate jobs are a guaranteed route to middle/upper-middle class.

I like the idea of passive income as I'm not sure how much longer my body will last in the army ( haha ) so I'm looking toward the future for my family's sake.