The house has some "hard" issues: 1. pretty steep hill in the front with stairs to the front of the house.

Check the states laws- depending on the strategy, you may not have to register.

However, it’s important to understand the loan’s key requirements:Owner-Occupancy: The borrower must live in one of the units as their primary residence for at least 12 months.Single Borrower: FHA loans are issued to individuals, not partnerships or entities, which means the loan would need to be in your name alone.Given your scenario, only you can qualify for the 203(k) loan since your partner does not intend to occupy the property.2.

I am not sure that I understand the title company's issue, as you are probably personally the Manager of the managing LLC.

Yep I look at it this scenario like issuing a hard money loan to myself since I recoup the interest in the 401k.

Without seeing your lease, if the lease says that 'charges are due as additional rent' the charges may fall into housing delinquency law.

Sewer issues in Chicago are very common which is why I ALWAYS recommend / almost require my clients to get them done + if there's trees in front or in the back of a property, there will almost always be plumbing issues + needed rodding. 

If you have any due- plexes, try-plexes, four-plexes or mother in-laws, please reach out to me.

Occasionally there’s really an issue but usually it’s a busybody who doesn’t like what the neighbor is doing.

Please note that I have 25 years of experience renting out apartments and houses in three other states, but I’ve never done so in MA, so I don’t have experience with local MA laws or vendor expenses.