From there, you can utilize that team to gain experience and understanding into the market.  

Otherwise many many many agents spend a lot of time and effort finding property and writing contracts only to find that the funds can't be transferred, or they don't have immediate access to the funds, or they need some kind of approval from 3-4-5th parties, or there are exchange restrictions, or 9000 other excuses.You probably need to find them a commercial broker who can handle whatever kind of investment they want to make. 

This first season is for you to gain hospitality and property management experience and reviews.

Generally waiting at least 3 months will allow you to use the new appraised value compared to the purchase price so if you've done renovations that will help with your LTV for either a refinance where you change loan programs or rates (a rate and term refinance) or a cash out refinance that will give you access to more potential cash for your next project.More info on DSCR loans: DSCR loans won't use your income to underwrite the loan.

It takes a lot of work to find a tenant, your commision gained from the income should only be for the services rendered while the tenant is in the home ( in my opinion ).Some additional fees I can think off, are maintenances fees, for larger projects that require a lot of management and research.

Even if it does appreciate, the only way you realize those gains is if you sell.  

I am going to get hit with capital gains and state taxes(Idaho 5.8%)..closing on cabin on the 18th of Nov.

How much and what would I do with the gain on sale, and how does that help or hurt my strategy? 

Different mortgage brokers and lenders have access to different loan programs.

Even though you feel you don't reach the full cash flow potential, you gain on making the lives of those families more comfortable.