It only has positive cash flow due to concessions by the seller that will last about 2 years.Property values have seemed to drop in that area, so I'm doing something different by requesting a reassessment of my property taxes.

Also, you should ask for an option period, i.e. the first 14 days of the escrow, so that if you need to cancel for any reason, you can get your EMD back. 

I recommend speaking with a tax strategist to discuss options to reduce your tax liabilities without becoming an S-corp. 

It's not unheard of, but I couldn't understand why anyone would want to do that given there are so many other options out there.

Exploring alternative options, I inquired about a property that was listed for rent.

So pretty good equity position within a year plus cash flowing well based on a $325k purchase price.

There are markets today, even with high rates, that are cash flow positive and do have great appreciation. 

I am not there yet, and hope to not have to go that route, but would be good to know all of my options. 

Make sure you have that addressed just from a liability standpoint. 4) You could also look into a mid-term rental option with traveling nurses if you think the unit is truly rentable. 5) AirBnB restrictions have gotten much stricter as well in general in Chicago, so make sure you are on the right side of those if you put your unit up since you are required to register with the City.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.