1st lenders in the area will not lend on a burn out. 2nd I am doing this project out of pocket essentially.

If there's anything I've learned over my entire portfolio, is that there are always more projects around the corner, they take longer than you think, and they're more expensive than budgeted.

Take it one question at a time and build out your analysis in a spreadsheet of your own.While you're doing this, speak with a mortgage lender or two who know investing. 

In my New England market I’ve been able to source some amounts of cash flow but my appreciation has been phenomenal and the projections for future appreciation keep me from selling to attempt to find better cash flow.

It's best for investors with a medium to long-term timeline and experience in development projects.

Many banks handling tax escrow accounts for mortgages have mistakenly thought there was one tax due twice/year or totally missed one of the taxes.Investors should research the SEV and the Non-Homestead property tax millage rates to project what the property taxes will be after adjustment.

Why do you think you've been stuck in analysis paralysis? 

Quote from @Marcela Hoag: Start with a cost:benefit analysis.

I have 5-6 people to manage the student properties (and new projects).

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.