Cash out refi and new loans

[Hudson Wikoff]

Long story, will try to keep it short with bullet points.

Goal: cash out refi with current primary residence, which will be turned into AirBnB, use $$ from cash out ($60-90k) to purchase 2 investment properties and our new primary residence.

We also in need of newish vehicle.

Situation:

I started a business last year in same industry I came from, so need at least 1 year of W2, thus waiting till Jan 2022 and file taxes to be able to claim my income.

My wife is looking to leave her full time job to come work for our business and keep it growing. 

Questions:

1) How will my wife leaving her job affect our ability to achieve our goal?

2) should we execute in a specific order and how will each affect our credit or ability to pull a new loan?

The order I want to go in:

A) cash out refi on current primary house

B) purchase investment house

C) purchase vehicle

D) purchase new primary residence 

E) purchase next investment house 

Thank you so much in advance for any input, Hudson