They didn’t use a comp 2 short blocks away that sold for 175k with a more similar lot with a large garage.

Because of this my short term summer returns rival the winter returns. 

In short the "Teacher" saught legal counsel, the "Wholesaler" didn't.

I'd like to know if any of the other investors out there mind sharing their experiences with short term rentals in the KC area, specifically in Midtown near Hyde Park/Westport.

I actively invest in short term rentals we took a different approach to it and tested it with our least likely to succeed property and have more than doubled our monthly income.

To make a long story short a relative has given me and my wife a large sum of money as a gift and we want to use this to purchase our first Condo/home.

That's a huge red flag to me, short of clearly showing reasons why.

The lender gives you a slightly higher rate, and THEY pay those costs for you.This strategy is a great short-term strategy, because most times it takes about 5-7 years +/- to break even on paying those costs.Which is why for many real estate investors, especially flippers, this is a better strategy, and one that I educate all my clients about.Everyone is so caught up in the lowest rate, when in fact overall cost-effectiveness and knowing the long-term plan are more important than rate. 

Basically, because my estimated timeline before purchase is 12-36 months then that isn't very long term and thus I wouldn't be riding the "general upward slope of the economy" but would rather be subject to whatever short term market conditions come my way. 

I purchased a single family in May '17 as my primary residence shortly before listening to BP podcasts and researching real estate.