The biggest hurdles, obstacles, and challenges in life that limit your belief and mental structure in no particular order:1)Thinking where you start is where you finish.2)People resting or stopping in the middle, not at the end. 3)Prioritizing instant gratification rather than delayed gratification4)The controversial mark twain  quote or not quote--It ain't what you don't know that gets you in trouble, it's what you know that ain't so.5) The lack of an ability to move on.6) Not appreciating the power of delegation.There's probably 2-3 others I am missing, but over time these have rang so true in any instance I have faced in life.

Echoing what Shawn said above, you would have a vast array of options ranging from lively resorts with tons of amenities (think water slides, lazy rivers, tennis)...ranging to quieter resorts with lots of green space and forest or lake view homes.

I was doing fine until I decided to go for a more expensive neighborhood and price range.

While a high limit of $500k or $600k might seem sufficient, there are situations where these amounts can fall short.

Multifamily has a wide range of property sizes, types, class etc.

Madison was always more of a college town, so it was not impacted the same way.And MKE has a wide variety of neighborhoods with very different ptice ranges, look up Whitefish Bay or Wauwatosa, they are expensive. 

I am seeing 11% on some more expensive reservations and I saw for at 16-19% in the $1000-2000 range. 

The prices for coaching seem to range vastly and it's a massive expense that could really put you in the hole.

I was asking which cities would have that price range of a Section 8 home, and would have that larger rent amount, to get that higher CoC returns. 

Ranging from cashflow based to hedging based.