Am I underwriting conservatively, accounting for higher interest rates, inflation, and potential market softening?

That will likely be one of the side effects of improving your property and should be accounted for in your analysis.

Where it gets interesting is that the house has 5 mailing addresses associated with it and the fire prevention bureau has on their records it is also a 5- unit house, and I am billed as such upon annual renewals/inspections.

Definitely consult with your accountant on that.

@Nicole GrazianoI recommend that you have a consultation with a real estate tax accountant regarding your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

@Steven HsuBigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

I specifically want to call out one of their Senior Accounts Associate, Charlotte Cunningham, who helped me through the process on my first purchase as I needed to buy a sizable amount of furniture quickly and she was able to help me make moves quickly...and didn't make me feel bad whatsoever when I pulled back a few items at the last minute I was able to find them cheaper elsewhere.

In this manual (which I assume could be modified to provide to tenants) I include all the financing information (which you would not include for tenants) bank accounts, mortgage accounts, payment information, and mortgage payoff), a list of the contractors, what each contractor does, a list of upcoming planned or necessary repairs, and a copy of all leases associated with the property.

Our average on these investments have been near 37% annual ROI.  

Dude has a few screws loose.Hey Account Closed do you got anything to say about this?