If you're working with a traditional bank/lender, getting your cash out quickly may prove to be difficult.

@Jason Shackleton @Roy Cleeves with my budget of ~$300k, It seems very difficult to find an adequate cash flowing property in an area known to appreciate. 

@Benjamin Seibert One of the things that is difficult for me to understand is the amount of equity in the property.

And while you can probably prevail, it will be more difficult without help.

Additionally, when I hired him I requested that he report any issues that would make his job more difficult (e.g. clutter to mow around). 

Land is difficult for a seller to get sold fast, the seller might carry a loan of half the price for like ten years, this gives you more cash to work with.Girlfriend has how many pets?

I've been trying to run the numbers for each scenario but finding reasonable numbers has been a little difficult.

@David DeAvila in this market, no, it should not be difficult to sell tenant occupied and is quite common.

My wife and I wanted to get into real estate investing and were living in San Diego, CA where buying a SFR would make us house-poor as properties with an ADU (accessory dwelling unit/granny flat) were incredibly difficult to find and expensive.Therefore we researched other out-of-state markets and decided to visit Colorado Springs, CO.

Beyond that I think you'll have a difficult time.