My family is in Chicago so I am curious to buy a place that I would live in when in town.

You'd need a JV partner and they would probably want to take control of that project. 

As a GC I can advise try to retain control of your finishing material orders (anything where you need to make a choice ((tile, flooring, lites, faucets, tubs)) vs. construction materials (2x4s, mortar, shingles)) because we get those discounts on the finishing items and we keep them!

Real estate prices always go upReal estate prices have always gone up over a long enough time horizon on a national average..... but yes, on a year-over-year basis or in a specific city or town your experience may differ 

If you’re taking over their payments but not transferring ownership yet, they may still have control of the policy.

My STRs are in a small destination mountain town and finding good cleaners is the #1 struggle. 

These areas might provide higher returns due to lower initial property costs combined with tax savings.Rent Control Laws: Be mindful of local rent control or tenant protection laws, which could limit your ability to adjust rental rates or manage your property effectively.7.

@Jason Fitzwater do find guest care more about being closer to the town of Blue Ridge and attractions like Mercier’s Orchards, or is Cherry Log/Mineral Bluff/etc. area still good?

Given I am in a college town and a lot of students find themselves between leases over the summer, during breaks etc.

Places like Liberty/Claycomo/Gladstone in the Northland, Blue Springs and the Eastern side of Independence, on the East side of town, Olathe/Lenxa KS on the SouthWest side, and more.