Often times you will pay much more in taxes than if you pulled the money out, paid the taxes and penalty and then started investing in real estate.For example, with the financing you mentioned, the IRA must pay taxes on the portion of the profit earned by financing. 

Even using dedicated independent contractors as your maintenance crew requires book keeping (bills receivable, payment, bookkeeping to track expenses for tax purposes and warranty claims, etc.).Having a reserve for cap ex, but not allocating any estimate for the cap ex cost means that your cash flow estimate does not include cap ex. 

Zachary,Your concerns about Cleveland are valid—high property taxes and stagnant population growth are definitely challenges to consider.

Hello everyone, I am reaching out to the BP Community for suggestions.My Portfolio100% owner of 7 SFH PropertiesGP in about 30 SFH properties(of which I own somewhere between 25% to 50%)All but two properties are managed by a PM CompanyNet worth of the above is about $2,000,000 - $2,500,000My IssuesI have many SFH's - Which take up time(Currently spending time paying property tax and insurance, requesting quotes on insurance policies and overseeing the PM Company(approve rent increases, approve renovation projects, etc).They also take up head-space(having to remember property addresses, remembering when property taxes are due)(I have reminders/systems but something I would like to reduce)Goals1) Spend less time on Real Estate2) Free up head-space2) Make $240,000 annually from real estate(Which I think is not to hard if I can increase my net worth and can get an 8% return)Possible Solutions1) Sell all the SFH's and buy 4-Unit Properties to take advantage of conventional financing2) Sell all the SFH's and buy one large apartment complex3) Sell al the SFH's and invest in syndications4) Sell all the SFH's and purchase stock / bonds5) Continue to hold all the SFH's6) Any other suggestionsOther Considations1) Should I consider private notes?

The IL property tax is a pain. 

By paying a commission and taxes, you get more money from the property by doing a Refi. 

This would end up getting you some tax benefits and extra cash flow that could help you leverage that into another property...maybe a 1031 exchange.

I've been buried with tax preparation and a couple projects, so BP moved from the back burner to completely off the stove!

The 1031 exchange is what allows them to do this without having to pay tax on the gain or depreciation recapture. 

I didn’t see your location in your profile or your post, but assume at least 17% state/federal taxes leaves you with $10k/yr.