So what would be wrong with CASHOUT refinancing if the property would still cash flow 300$ a month and I deployed the cash into another primary (looking for property’s under market value, in hope of being able to repeat process again every 1-2 years with forced and natural appreciation?

I currently own/ operate 2 STR's in CO and if you enjoy beautiful hikes, mountain homes, skiing, and amazing nature views overall, it may be the place for you! 

I know all the debates of throwing money away on rent vs owning but for someone like me who doesn't want to be locked into anything it makes more sense for me to rent.Personally I think in the future people will require more flexibility in their lives with things like gig economies, rapidly changing technology and the nature of work, etc, so this could even be a growing trend over time.  

My goal is to cash flow 10k/month before I retire to help supplement retirement.

For example, the energy sector is rebounding as we are now seeing oil jump above $75 a barrel and Natural Gas is now over $3. 

I was astounded at how well the coloring matched the natural stone and other finishes in the house and pulled the look together so fantastically.

the LLC is in the of "Carter Properties, LLC" ( nature of business: managing properties).

You'll find modern housing units, apartment style billets, family housing and the Navy did an extensive study of natural ventilation and cooling for tropical areas.

Are you trying to find a place that will cash flow you nicely each month or a place that supplements your payments and is nice to live. 

It is natural and expected.