While you don't need an accountant for this as you can do your own research, and accountant can cut the research time in half, remove any noise, and tell you how that strategy can apply to your personal situation 

We needed a new well pump installed on our shared well in 2022 which was ~$11k for our half.

I think the easiest way to find the right partner is to find one that you are aligned with as far as investing in rental properties.The other option would be to keep flipping properties until you get enough money for a down payment on a rental.Another option would be to look for a BRRRR (buy, rehab, rent, refi, repeat) because then your friend could still bring money to the table and you could pay them back their portion plus interest and then you keep the rental property.What area of Chicago did you do your flip in?

My "moving" consists of half riding my bike, half bodyweight exercises like push ups, pull ups, body squats, planks.

It appears they restructured to actually do more flips my buddy has a decent social media presence and is boasting about his last two flips and the profits are about half of this one and required 1 million in capital.

If you are crazy enough to carry debt on them that comes out of your half.

1. probably the easiest and least complex options - also should not be really any more cost than opening a single member entity tbh...ensure that dissolution clauses are properly drafted for you both being on title2. for one rental property, this is overkill (although there are many people that will say you need to do this...the maintenance and cost of a trust for one rental property is likely not profitable) 3. personal name with good insurance policy if you're worried about liabilityHappy to go over ideas.

I haven't payed anything upfront so it is not a money issue, more the fact that there are half done jobs left behind and another gc for sure will quote me more to pick those back up.

We had an 8 figure LOC to buy distressed assets and sub 2  half of it completely unsecured so check book.

I'm guessing it would be easiest for them to come two weeks before their move in date and get an Airbnb and tour different options and make a decision quickly like you said.