Help advice vacation rental buying

[Derek Larson]

I have been wanting to have a rental property for years, or even vacation rental. My wife has been onboard with vacation home for a couple of years. It is in a place where we want to retire. (15-20 years from now). About two hours away. It is a hot place for vacations especially in summer. We would like to use it personally more in winter ourselves, but some summer too.

We just moved back to Midwest and bought a cheaper house so we could have more cash to do this investment.

Debt free except 150k mortgage

200k in bank and our retirement is being funded 15%. Every month 2,000 dollars left in budget.

Am I being too conservative not to jump right in and let the chips fall where the lay?

How easy is it just to rent out a home like this just to pay for overhead expenses.

On a lake will probably cost about $300k.

How do I start? with a property managers or Realestate agent?

Any advice or additional questions I need to ask myself would be helpful.