In my experiences, it really comes down to the tenants that create either a management headache or a super easy investment.

Actually in Pewaukee, so also easy to get to from Madison.

It is counter-intuitive, but more expensive homes is much easier.

@Chris Mahoo many new investors don't take the time to properly understand RE investing.1) Many are using approaches from 2010-2018 when Class A property prices were so low from the Great RE Crash that an investor could cashflow and get pretty easy Class A tenants to manage.2) If you look at what investors were doing before 2008-2010, most were buying Class B & C rentals.To make it worth while, an investor either needs to Fix & Flip or invest & hold rentals for 10+ years.- Over a 10 year period cashflow will increase as rents increase (rents typically rise faster than property taxes, insurance, etc.)- The property should be appreciating, if purchased in a good location, increasing the owner's equity/wealth.- Rents will be paying the mortgage off, increasing the owner's equity/wealth.- If you hold a rental until death, you can pass it on with a stepped-up cost basis, limiting captial gains if then sold (limited by inheritance tax limitations).Too many newbies on this site trying to replace their day job income via "passive" real estate investing w/o digging deep enough to understand how it really works.

One more reason why people should stop looking for the easy path to building wealth.Increase earnings, reduce expenses, save, and invest.

You might make less, but you cut a lot of costs, make the 1031 exchange easy and maybe worthwhile. 

I also know finding a quadplex as a first property in Orange County isn’t going to be easy, but I’m open to hearing people’s thoughts.My goal isn’t to turn a profit right away—I know properties here might not have positive cash flow for a few years.

That it is near you is good, but find out how easy it will be to sell. 

After 35 years I’ve developed a healthy respect for this business from the school of hard knocks.The day I’ve discovered this business is easy or simple will be a good day to retire.

Fees should be clearly stated in writing, easy to understand, and justifiable.