I'm gonna go out on a limb and say the first-time investor isn't looking to spend $2M and be in the black $1,000/mo or more.Secondly, and most importantly, you can NOT get an STR in Breckenridge (or Keystone, another option in your response).

I know that co-star offers this, but I don't have that budget, I am okay with spending 100-200 a month for software to practice with and learn.

What did you spend on rehab?

If you find something, go hard money and then spend the next few months re-leveraging the existing debt.You can have your cake and eat it too, just be patient my friend. 

Spend time and be strategic - but also make sure you're moving forward and not getting hung up on things.

If you have less than 500k to spend, it's near impossible.

I am embarrassed to admit how much time I have spend on these and I only have “2 doors”But I can say I used both Stessa and Landlord studio a lot so can actually be helpful here.

We spend the summer on a small lake off Winnipesaukee but we don't own it.

RE is a long game, and congrats on having $250K in cash to spend!  

This allows you to spend more time focusing on your investment.