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!

[Jason Muth]

Hi Alex - I found myself in a similar position when we bought our first investment property in 2016.

We went the Airbnb route, and now have 3, with a 4th being built as new construction.

Decided on markets about 1.5-2.5 miles from Boston, where we live, and they ended up being both cash-flowing and appreciating markets.

Not to say that you should go with STRs. Just saying that it's an idea if you do your homework, build your systems, network with people already doing it, are willing to invest some hand-on time while you learn the space, and get a but lucky (regardless of how prepared we are, luck is always a factors in anything we do, isn't it?)

Fast forward to the end result (well 5+ years later), and looking at my portfolio of assets now, and I feel very comfortable in how diversified I am. The troubles in the stock market that impact my retirement accounts so far this year haven't been fun, but they certainly have not been devastating because my real estate is acting as a counterbalance. I wish I had figured this out a few years earlier. But I've doubled my annual income in that period without relying on raises from my W-2. And now we have a ton of tax benefits from the investments.