1st investment property as a vacation home for personal use/STR

[Alex Duncan]

Hello!  I am new to this forum, found it via the podcast and very excited to see all of these resources and advice available.  Over the last several months, I have been reading, listening and studying up on financial independence.  I am 38, I have a successful career in medical device sales management and have a relatively high income of $250k+ per year.  I really enjoy my job but it is extremely demanding and leaves little room for much else.  I am here because the concept of becoming financially independent through real estate is easy to understand and appealing, I at least have some experience in buying and selling 4 different homes (all primary residence) and I can have some level of control in the outcome.

I have a decent amount of capital available, about $300k liquid (that would require me to sell a few stocks/ETF's), I have nearly 50% equity in my house valued at just over $1M, and a healthy 401k etc.  My wife also has a decent amount of capital but we keep our finances mostly separate, and she is very conservative with her money.

I am ready to buy my first investment property, and I want this to be a property used for personal use as well as short term rentals.  Looking in Grand County, CO, likely Winter Park, Fraser, or Tabernacle (I live in the Denver area).  Likely a 2/3 bedroom condo.  I had a great conversation with a Realtor in the area today and am learning more by the minute
I also saw there was a thread on here dedicated to Grand County that I got some valuable information out of.  

Given all of the information I have shared, how would you go about doing your research to make your first investment as successful as possible? Basically, what would you do if you were me?  I realize this question is a bit vague, but appreciate any guidance!