When to sell properties

[Chris Allen]

When Do you think the best time would be to sell off a small portfolio? 

long story short, I will be starting grad school next year and will not be able to work while in school for the next three years. I am wanting to sell off my 4 properties and use those proceeds to help fund the next 3 years of living expenses for my family and I. 

Question is, should I go ahead and sell off all the properties now while I am still have a job and sell will be reflected on 2024 Taxes, them 0 income next 3 years. Sell them all off next year when my earned income will be $0, or try sell Mayne 1 or 2 now, and then the other two next year? 

I would immagine from a tax perspective, next year i would be in a much lower tax bracket, but then i am not sure if i might be missing something in regards to student loans, etc...