“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?”

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

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

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. 

I would refund especially if you rebooted for those dates.

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.

There are 20+ Tax Pros on this forum.

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. 

You get all the benefits of owning real estate (cash flow, appreciation, tax benefits) with none of the headaches of buying, renovating, or managing properties.

I am selling my current business and will have about 300k that I would like to avoid paying taxes as much as possible on, so I am looking for something to invest in.