Quote from @Galant Ant: Permit delays in NY can derail timelines and budgets for developers and flippers.

My first flip was a HUD foreclosure with no money down—far from perfect, but I learned a ton about budgeting and contractors.

One thing I did note is my insurance is $3K a year lower due to the monitored fire suppression system in these larger properties versus my smaller properties that sleep 12 or less built close to the same time.As someone who has lived in Illinois twice, the politicians there don't care if people burn as long as they can tax and spend. 

Get to a point of having enough cash flow for me to spend less time on my job and more time with young kids in 5 years2.

Are they holding the money, or are they spending it?

I would base your answer on buying the bigger one (within reason) that will fit in your space that fits your budget.  

Not spending money.  

But if they spend more than 5 minutes looking at the SB rental market, they will likely see that they are in a great situation and won’t fight too hard.   

Personal background: Married with no kids, 100% debt free, live a rather tame lifestyle and don't spend large amounts of money, two newer vehicles (2020 & 2024) so no vehicle purchases expected for the next 10 years. 

Quote from @Galant Ant: Permit delays in NY can derail timelines and budgets for developers and flippers.