STR's are currently not allowed unless you occupy the property.

On the plus side the rare times a Section 8 tenant moves the unit is in rent ready condition because it hasn't been ignored as occupied for 6-10 years.

My question is, can I use SB9 on my property that is currently occupied by tenants?

Also, when not occupied, the PITI on a high-end home can quickly erode prior cash flows.

Or else reduce enough on price to deal with an eviction from an illegal unit.I don't know Chicago laws, but in NYC if you have an illegal unit, the tenant occupying it seems to have more rights than the owner does and doesn't have to pay rent... 

I went owner occupied either conventional or FHA.  3-5% down at the time you only had to live there 1 year and then you can move out or move on. 

@Nicholas A. your shotgun approach has a high probability of getting the exact quality you put into it.95%+ of real estate agent, many of them posting they are "investor-friendly", only know how to deal with owner-occupied transactions. 

Four of the five units are occupied, and starting in month one, this property will cash flow substantially more than the house I sold to buy it.

On my street, only about half of the homes are rebuilt, and about half of those are occupied by the pre-fire owners. 

Just read under Occupancy: https://www.benefits.va.gov/WARMS/docs/admin26/handbook/Chap...All the VA says is that you must intend to occupy the property within 60 days, and there are even exceptions to that.