Aside, what I don't know (and would like to know if anyone has tried it) is what happens if the companion unit is attached to an existing duplex - not sure whether that would trigger commercial requirements (MEP plan, fire alarm monitoring, etc). 

I always thought lending would be easier than managing residential rentals, but I figured the legal process to achieve it would not be a do-it-yourself prospect.

I need to get better at analyzing deals so I can figure out if my cash flow goals are achievable.

The work was done extremely slow and now that we have been back to see it the hvac closet it full of trash and debris from their work and the unit is still not performing as it did for the 6 years before we rented it out.

I realized I need to put action behind my words in order to achieve my dreams.

Hotel To Condotel  LoanProperty Status Rehab Mode Approx 50% Of Units CompletedCurrent Purchase Price $7 million$7 million/130=$53,846 per unit purchase priceNearby Rental Income Per Unit Is $1,280 per month$1,280x130=$166,400 Gross Monthly IncomeGross Yearly Income Is $1,996,800Gross Income Over Life of Loan With No Rate Increases $59,904,0008.5% LTV $59,904,000/130=$460,800/360=$1,280Average Daily Rental Income Amount Insured $43.64 Loan Amount: (75% of $7 million) $5,250,000 Loan Interest Rate: 7 % Loan Term: 30 years Monthly Principal: $14,583.33 Yearly Principal $175,000.00 Monthly Interest: $30,625.00 Yearly Interest $367,500.00 Monthly Tax Amount $7,583 (130x700) Yearly Tax $ 91,000.00 Number of Payments: 360 P/I Cumulative Payments: Yearly $542,500 Lifetime of Loan: $16,275,000 Total Interest Paid: $11,010,000 Use of Funds: $1,250,000 million to investor/owner$ 4 million used to cover monthly expenses for 48 months while conversion is completed

The unit is already damaged so why not keep the tenant and just charge her more?

The garden unit is almost turn-key but we want to utilize the mid term rental strategy while we house hack :) Chicago seems like a great place for this strategy especially for newbies like us. 

My name's Mohammed (Mo), I'm an investor and realtor that's looking to be around likeminded people who want to keep each other accountable as we achieve our RE goals for 2023 and beyond. 

@JD Martin  I never said anyone else's opinion was invalid and I appreciate points of view from all sides but what I hate to see is when everyone tries to poo poo someone's idea and dissuade them from achieving their dreams.