Eventually, I would retire in this house after 20-25 years.Thanks in advance for your response.

Just think of what you can accomplish in 10-15 years before you "retire."

Most convetional and FHA uderwriters want to see 2 years of stable job history.

Also, Sheboygan has the most middle class households of any metro area in this study: https://www.pewresearch.org/fact-tank/2018/09/06/the-american-middle-class-is-stable-in-size-but-losing-ground-financially-to-upper-income-families/.Happy hunting!

I would stick to the more stable suburbs where cash-flow is steady. 

I thought of the idea of getting my parents to buy real estate in the area they want to retire in.

I have properties that I'm selling to buy REIT mutual funds as I'm nearing retirement (don't want to deal with the hassles).

I have a project up in Napa Valley that is a BRRRR for a STR and eventual retirement place to generate cashflow and I'm trying to find a team and location out of state to look for doors.I think you could do either and be successful but it comes down to what do you really want? 

Also no equity in this home that’s why I intend to move into it after I retire from military in June.

Not to mention that the economy and job market is really stable here.