We use DealCheck to underwire and QuickBooks Online for everything related to accounting and numbers.

The entire reason I hired a company is they are the experts and I expect them to take full accountability of making sure I am in the know and 100% compliant.

This is really a better question for your accountant first because it depends on what you are trying to offset.

It's a strategy that has proven effective time and again.Five years is a solid timeframe to account for market fluctuations and ensure profitable sales.

We would meet once a month and just hold each other accountable for the steps we are all taking in building our RE business. 

The best strategy depends on your goals, but here’s a breakdown:Selling outright would result in paying capital gains tax and depreciation recapture, but since the appreciation is minimal, the tax impact may be relatively low.Gifting the property to your son could potentially allow him to sell it with a lower tax rate, but since he hasn't used it as a primary residence, he won’t qualify for the exclusion of capital gains tax on a primary residence, and you'd need to account for gift tax implications.1031 exchange could defer taxes, but you would need to purchase a like-kind property of equal or greater value and meet all the IRS requirements.

But with this being a 5 unit multi-family building most lenders do not offer a loan product that will take the STR revenue into account. 

However, after running the numbers accounting for insurance, PMI, taxes, vacancy, capX, property manager, etc. the property is estimated -1.85% cash on cash return (-$600/mo) once I fully rent the property.

@Edward SegaarBigger Pockets is a great place to find a real estate accountant. 

I have a US credit score, US bank accounts and some US-based income, but my paychecks are not.