If the building is currently recognized as a single family residence,  then you are changing use and presumably will need to sprinkler the building and satisfy other fire rating and STC rating requirements not to mention the added costs of having to run mechanicals for multiple units, multiple kitchens, additional bathrooms etc.  

For example, hotels or short-term rental properties like Airbnb often generate more income than traditional apartments, especially if the location supports it.Entitlements and Approvals: Check whether your project fits within the land’s current zoning (by-right uses) or if it will require variances or rezoning.

@Charlie Martin Buying under an LLC offers liability protection and separates business finances, but it can complicate financing with higher rates and stricter terms, and lenders may still require a personal guarantee, impacting your DTI.For your first property, consider purchasing in your personal name for better loan terms and transferring it to an LLC later if needed, while using strong umbrella insurance to mitigate risk.

Create a simple spreadsheet or written list to compare the features of each and identify the ones that align with your requirements.

It likely will require years to achieve cash neutral.  

Can you share what kind of proof you will require tenants to provide when they claim their pets are service pets/ ESG, will there be any different proofs between Service Pets and ESG? 

IF you were to renovate a non-conforming unit, that unit would now need to be brought up to code.When or if you rent out the unit, you, of course, run the risk of the tenant calling the city and saying the property isn't up to code, which would, in turn, cause an inspection by the city and likely result in some violations that would require you to bring the unit up to code.These types of units are ALL OVER the city of Chicago and be rented out on a daily basis, but there is still clear risk associated with renting them out.

As a general rule of thumb if the property has a ground level commercial requirement in order to show sufficient hardship to seek a residential use change the property should be located in a location that is not conducive to commercial use i.e residential street, close but not as marketable as properties located on neighborhood's primary commercial corridor etc. 

It wasn’t a detailed plumbing drawing- he had shown one line going to all units while the contractor pointed out that it is better to show individual lines to each unit as repairs and maintenance are easier. and some towns even require it . 

I know the 2-step authentication process is not a requirement because I've never had to do that so maybe you chose that when you set up your account?