Here are my considerations:I will be leaving my current job in the next couple months and pursuing a career switch, which could take anywhere from 3 to 8 months (maybe more). 

That is real money leaving your bank account.

I found out the caterer would leave if I had to do that, they would be without a bathroom and lose a lot of space (they used as an "office").

To those in the BP community who took the leap what have you been doing since leaving your w2 job to help supplement your lifestyle on top of your investments/flips?

I know the house next door to me is a rental, as are two or three other houses within a hundred feet of me, but only one of them is listed as non-homestead on the Hennepin County GIS map.Do I have to convert this house to non-homestead when I start renting it, or can I leave it as is? 

If it is a large raise and the tenants are good you can do it stepwise but if they are going to leave they will still leave so you are prolonging the inevitable.

One is on his 3rd year and says that he'll never leave and the other is on his 9th year.

She paid all of the $2400 deposit herself and felt the need to leave so bad that she has left with the knowledge that she may lose the full $2400.

They leave when they choose regardless of a lease.

Now that it’s getting close to the time for me to leave, I’m rethinking my strategy.