Quote from @Salil Surendran: You MUST convert to landlord insurance.

Purchase price: $325,000 Cash invested: $150,000 This was our first primary home and was converted to rental after living in it for 10 years.

If you are using STR, REPS, or self rental with material participation to convert to active or nonpassive income, you do not have to do this if you have passive business invesment that produce passive income that will exceed the loss generated by depreciation.

I found what seemed to be a great property with a house for an STR and other space that I could expand for camping/RV sites and a barn that could be converted into a venue for events. 

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

If they don't, the document says their consequence is that they will automatically convert to a month-to-month rental on [DATE] with a 25% increase to their rent.

Conventional 5% Down Loan (Owner-Occupied)If you live in the property for at least one year, you can use a primary residence loan with as little as 5% down.After a year, you can convert it to a short-term rental (STR).Loan types: Conventional (Fannie Mae, Freddie Mac)2.

If, through the process of renovating the property, the market shifts, do you have an alternate plan for the property, whether it be to live in it until the market improves, or convert it to a rental property, etc. 

I am going to talk to my CPA and see if I can convert.   

If you convert a main home to a rental,  you do not get the full $500k exclusion.