I do like to start with open communication but if a tenant does not appear to be interested in coming up with solutions I recommend using an attorney right away. 

Combine that with SS income (maybe?)

I live in FL, so no state income tax.

My current rent is $2300 at my apartment and I'm assuming the $2300-$2500 liability will be consistent in this property given the Purchase price, interest rate, and including rental income of $2000-$2200 of the other unit.

Your rentals should only perform better over time as rental income increases faster than property taxes, insurance and other expenses.How much will that contribute to your retirement income?

They always have capital outlay for months (sometimes many months) before any income (time value of money).  

I am scared to pull money out of my home unless it is generating income in which it will this year.

If the appraiser believes the income approach is necessary for credible assignment results, then the income approach must be included.

Also is the $41,255 NOI or is that just income?

These plans are beautiful inventories of zoning, demographics, income, traffic patterns, etc. but now what?