I found a 3-unit property for $629K on the west side of Chicago (Wicker Park area) that will cash flow.Issue is that the foundation is settling and will need to have a significant amount of work done according to the sellers agent and the inspection that they had.

Please double check this and make sure that wasn’t the amount for the raw land prior to the build.

Ease of working with owner = easier for you to cohost --- some owners micromanage and 2-3x the amount of work for you for no reason.

What you can't do is adjust that amount to different tenants because if you gave it to someone else for 1725 or less even though you said 1800 and them NO to them for 1725....do that enough times and that may cause them to think you are discriminating against sec8 tenants.

My suggestion would be to cap your utilities at a certain amount and have Tenants pay anything over that amount.That will help you manage your expenses, and also allow Tenants to gage their usage each month, and make adjustments if they don't want to go over the allotted amount.As far as collection, provide the bill showing any overages and just have them pay for it along with their rent. 

For example, if the lender uses an 80% LTV on the loan, but the DSCR is 1.10x (and their minimum is 1.20x), then they will reduce the loan amount until they get the DSCR to 1.20x.

If you know that something major will need replacement in the future, increase the monthly amount you are depositing into your reserve fund.

With the new landlord/tenant ordinance that allows the tenant and extended amount of time to renew, this has encouraged prospective tenants to lock in leases for Fall 2022 term starting as early as last November.

Or maybe when I meet a certain amount of company revenue. 

In your case, changing the property from a rental to your primary residence constitutes a change in use.The depreciation recapture will be calculated based on the fair market value of the building at the time of conversion, not including the land value.Since you're tearing down the existing structure, the entire amount of depreciation taken over the past two years will likely be recaptured, as the building's value at conversion will effectively be zero.The recaptured amount will be taxed as ordinary income, up to a maximum rate of 25% for residential rental property (Section 1250 property).