What paperwork should I keep a paper trail of to make things like taxes and other situations better/easier for myself?

This is the BEST $100 you will ever spend, and if you listen to Amanda Han's tax book, you'll know it's also likely a business expense for you to write off :) https://biggerpockets.supercast.com/My perfect way to learn from the BP books is to listen to the audio book through the subscription above, then books that really stand out to me I go old school and get the physical copy so that I can re-read it, take notes in the margins, and put post it notes so key points are easier for me to re-reference in the future.

Working on large-scale data is great b/c sometimes it's all about how many owners you approach daily; the issue with over-the-top details is also getting lost in targeting specific owners and situations, aka focusers/tax liens, etc.

You get to harvest the equity tax free.

I'd love to move into another fixer upper for two years so we could flip tax free or live in for long enough to use our FHA loan.

Everything I bought is up 2-3x and last year I had net rental income on my taxes of $86,000.

Approximately 6-8 weeks ago my attorney stated he was unable to get the delinquent tax 'owner' nor the squatters served in this matter. 

This allows you to use all of the tax and deferred depreciation recapture to purchase the larger MF propertyA consolidation exchange is where you sell multiple investment properties to purchase a larger and nicer investment property, but you also get the benefit of using all of the tax you would have had to pay to your advantage.

Open to all suggestions.I would visit Columbus and consult a real estate attorney.

Our avg monthly expenses with reserves is around $1500 (mortgage, taxes, insurance, utilities, reserves ect).