What documents are needed for me to claim this on my taxes? 

A cost segregation study is one of the most beneficial tax benefits for commercial real estate properties.

Are there conflicting tax issues because the real estate agent is a member of the LLC? 

Adding an umbrella policy could boost your liability coverage, but it won't replace landlord's insurance.

“Am I happy enough with what I can make off of this property between cash flow and appreciation and tax benefits that it is worth my while?”

You can take the allocation for the unit you lived in tax free. 

We used tax returns, work bonus payments, any extra money for down payments and for renovation. 

if I could find a deal at $300/month profit after principle, interest, taxes, insurance, and a $100 maintenance reserve I would say it’s worth doing now (ie.

Conventional mortgages require higher FICO, reserves (money set aside to pay the loan), tax returns...just on that note, they typically won't count any income from the property rents until that money hits your tax returns for 2 years. 

There will be expenses you will have to maintain sure but the appreciation, tax benefit and rising rent/mortgage pay off make it a no brainer.