Computers can analyze property based on subjective data (square footage, # of beds/baths, etc.) but cannot calculate for objective data (quality of kitchen cabinets/counters, size of bedrooms and bathrooms, view out the living room window, etc.).You should study the market yourself.

You could sell the property at the beginning of the year and buy a property/place that property in service (and do a cost segregation study in the same year). 

The brightside of this is I will take way more time in researching, off your recommendation I went on youtube and have been studying till 4 am after work and have made up some Excel pages to really put down what's really going on and I noticed that a lot of what people are talking about is what I'm doing the only thing that I need to work on is my pitch, confidence when talking and overral experience.AND THANK YOU!

A cost segregation study will help maximize these properties depreciation expenses in the early years.

Lot less multifamily which is why I haven't bought but it is where I grew up.Make sure you study the eviction laws, I believe tioga County (but could be a different close county im not sure) my lawyer told me that you now HAVE to pay to pack up an evicted tenant professionally and store it for months at your own cost if they leave their stuff behind.

Here's an article with additional FAQs on cost segregation studies that you may find helpful and should answer some of your questions above. 

Study the market.

I do not desire to be a flipper.Because the rent to value is at all time worst (according to 2 recent studies) and because San Diego is a poor cash flow market, better cash flow is available in other markets for new purchases compared to my market. 

Study the market.

My vision includes developing the land into a destination with features like driveways, walking paths, utilities, and unique lodging structures.Here’s my tentative plan1.Place the existing STR in an LLC2.Apply for an SBA small business loan to fund the next steps, including a feasibility study (~$10k+), land clearing, and infrastructure development.While this direction excites me, I’m torn between pursuing this venture and continuing with a more traditional approach—buying one home per year using conventional loans.I’d love to hear your thoughts:•Has anyone transitioned from STRs to glamping or similar ventures?