Does it need repairs or a full replacement?

Didn't really put much into it besides painting the units and replacing things as they broke over the years.

Is there a smarter (tax-wise) way of leveraging the equity in the house?

Going on the first face to face with a seller in years, even after getting 2 deals to the table, this one was tough.Stating the obvious, there is no replacing "the number" but I literally didn't have it in me to say it at that moment.

@David RobertSevere nicotine damage can require extensive cleaning, sealing, and even replacing drywall or HVAC ductwork.

Quote from @James Wise: Quote from @Zack Whiting: Hello Bigger Pockets Community!

Instead, as with a lot of south Florida wholesale deals- we ended up replacing and having to fix things that were covered up and two years later she was ready to go.  

Never replace anything that can be patched together. 

I had a house near Augusta where the property manager charged 50% of what we asked for rent wise whenever we would get a new tenant as an aquisition fee, but Joan just does the 10%. 

I want to work my way into anything full time because I have a decent job now but eventually i want to have real estate/construction replace my income.