So, I don't mind paying more for better class properties and working to reduce debt and increase cash flow over time that ultimately will contribute to, but not be my entire retirement income.

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

Luke, Ultimately Boulder is a very good rental market.

Finding a good mentor can help, education helps, sources like BP can help ultimately action is required.  

Thanks for the breakdown - very helpful.In regards to how lenders look at the rent - I'm ultimately wanting to make this a Mid Term Rental if I hold it. 

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

Ultimately, we've decided to hold off and pay down our outstanding debts and save for a cash down payment on our first rental property.

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

My main concern is regarding cost-basis and future capital gains tax when I ultimately sale the property. 

Remember, if you have a contract and can't ultimately assign to a third-party, you're still responsible for closing on the deal unless you have a way to terminate the contract prior to the closing date using a weasel clause.