Mom barely made it through highschool, my dad died when I was six, and we lived below the poverty line until I was 14 and she remarried. 

That’s your new basis and assuming you have lived in the subject property for 2 of the last 5 years then you would be eligible for the $250,000 deduction unless you have remarried then it would be a $500,000 deduction.

Most recently, I flipped a home after getting remarried in 2020 for a $30k profit.

I am now remarried and my current wife never resided in the old house. 

She passed in early 2014 and my step dad stayed in the home and remarried within a year.

Her husband passed away, but she has not been remarried. 

Neither of us has remarried. 

Nothing has changed.If your mom has not remarried when a residence is sold or exchanged, the surviving spouse's period of ownership and use includes the period your dad owned and used the property.Mom can use the full $500,000 exclusion if (a) the sale occurs not later than two years after the date of death of the spouse, and (b) the rules permitting a maximum exclusion of $500,000 were met immediately before the date of death (including ownership and use by the dad)

I'm now remarried and my awesome wife has three kids of her own around my two kids ages and all five are doing great in school and life.

I can now foreclose.The couple divorced and remarried, neither live in the home I sold them.