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

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.

Does anyone have any good recommendations on books or accounts I can follow or read to learn more? 

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

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

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. 

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.

I have kept track of all my expenses in an excel sheet/word document but feel like there may be a more organized and efficient method to tracking?

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