I was playing with the idea of selling my condo, taking 300k of the equity to put a down payment towards a house listed at 660k.I'm assuming the reno will run $300/sqft and going in with the assumption that phase 1 will run 750k (figure the expansion of the house will have to wait) for the gut reno.I assume/hope (but definitely not banking on) that I will be able to refi in 2-3 years at a lower interest rate; if not for a lower rate.This will likely be a family home for the next 5-10 years at LEAST so investment value isn't quite at top of mind ATM.Questions:Even if it's not for lower interest rate, do you feel it's advisable to refi to remove the 203 loan in the future?

It will be remote, but since you live there now, you probably already have connections who either already know the house or local friends to find you good people to service things as needed.  

People are not choosing the cheapest housing available.

House hacking is financially a no-brainer and no city in the US (including Chicago) has more duplexes than Milwaukee.

My wife and I purchased a home at the very beginning of 2022 and "house-hacked."

We would buy this house all cash. 

I'm having a very hard time with them and on the verge of losing my earnest money on a house purchased to flip.

Quote from @Scott MacComb: I am doing my first true house flip (have remodeled plenty of houses for rental) and am trying to figure out a contract to use with a new general contractor whom I have not worked with previously. 

I'm from Leesburg, and I can tell you—multi-family is a solid choice (piggybacking the previous comments which I agree 💯), especially with that live-in/rent-out, house hack strategy.

Hurricane Milton recently caused widespread flooding, yet this house remained unaffected.