For example, a property in San Diego may lose $500 per month ($6,000 per year) but gain $60,000 per year in value, making it worthwhile to "lose" money each month in exchange for long-term gains.I recommend you start with BiggerPockets Ultimate Beginners Guide (free).

Best of luck with selecting your market—there's a wealth of knowledge and supportive investors here to help guide you along the way.

Start with BiggerPockets Ultimate Beginners Guide (free).

Start with BiggerPockets Ultimate Beginners Guide (free).

Stay hyperlocal and get a good team in place locally so you can recognize good people when you find them. 

Glad you introduced yourself.. have you identified any mentors who can guide you on your journey?

So, if anyone can guide me in the right direction, I would like to know:1.

I am torn between pricing rent lower with a minimum 3 night stay or just weeding out the less desirable/more work clients with higher pricing.  

Here's a https://www.irs.gov/businesses/cost-segregation-audit-technique-guide-chapter-4-principal-elements-of-a-quality-cost-segregation-study-and-report to the IRS website noting specific items that are included in the cost segregation study report. hmm, that website is a 404 error.  

Start with BiggerPockets Ultimate Beginners Guide (free).