They can't assess all the subjective data like overall layout, view from the living room window, the dogs next door that bark all day, the width of doorways, size of individual rooms, quality of kitchen cabinets and appliances, etc.The best thing to do is study your market regularly.

But, I'm fairly risk averse, and do live in a heavily tenant leaning area as far as regulations and court judgements. 

I have a waiting list for tenants as my rentals are all where people actually want to live.

If you are doing a live-in flip why not use that equity for a down payment with a refi or HELOC?

Quote from @Fernando NA: Hello everyone,I’m considering purchasing a piece of land near Divide, CO, to build a small off-grid log cabin and list it on Airbnb or similar platforms.For those of you who live in the area or have experience with this, I have a few questions:>Is it possible to list such a property on Airbnb given the local regulations?

Selling would likely trigger capital gains taxes (unless you lived in the property for two out of the last five years or use a 1031 exchange).

I got tired of paying to live in other people’s homes.

It was a small $$$ project but time consuming because that was something I DIY'd while living in the property. 

Ko,The property is in Missoula Montana, I live in Bozeman Montana. 

Since you are living in the property, you probably have developed relationships with an electrician, a plumber, and a general handyman, if you haven't reach out and meet a few now, while you are in the home, so that you can easily make a call or two when it will be necessary.