When house-hacking with 5% down, returns on cash invested could be huge when you factor in the appreciation gains.

I can see things moving forward in two ways: 1) These individuals and entities will work with us to return monies owed back to the Company or 2) we will need to go to litigation.

Also to risk adjust the returns.  

How much time should I realistically allot for application/background checks, walkthrough, paperwork return, deposit and first rent collection? 

Correct, however 1% is NOT going to provide you with a good return.

I would discuss financials on this if you choose to come see the pre-rehab on Dec 1 (I have made a lot of money (close to 7 digits after this rehab is done in ~2 months) but due to not executing a cash out refi (due to the rate increases) my return is below my underwriting).

In terms of Costs associated with an LLC-Roughly like $100 to file with the secretary of state in Ohio if you wanted to do it yourself-Cost for your accountant to prep a tax return at the end of the year for that LLC (depends on your accountant)-Cost of a higher interest rate with a DSCR loan -Maybe more advanced, but if you have more rentals the cost of additional bookkeeping software like having to pay for additional quick books accounts.

Typically in Kihei the 1 beds offer a better cash on cash return but if you need a 2 bed for personal use that would make sense . 

The expected returns are a mix of cash flow and appreciation, ensuring short-term stability and long-term wealth building.Good luck!

I personally wont buy a property unless it has a minimum 40% Cash on cash return.