The area doesn’t start to improve until you reach the United Center.

That has property tax consequences.The more improvements on the land (which includes fences) the more important a survey is.

With these changes, the portfolio is now expected to be about -$2,300 / month cash flow.I am considering a few options and would love this communities opinions:Option 1) Sell property 1 to pay entire mortgage of property 5 (highest interest rate) -- Pro: Improves cash flow by ~$1,600 / month. 

These updates modernized the property, improved its curb appeal, and significantly increased its market value.

I've also considered asking if the owner is interested in an assignable contract, I see hige value add here from the deferred maintenance that I personally can handle and coordinate to small improvements and raising rents slightly.

Your best bet is doing a DSCR cash out refinance with no seasoning if you can show you improved the property.

Plus, you could potentially get better interest rates and streamline your loan payments, which would improve your cash flow. 

Hi Nicholas,When thinking about taxes and deductions for your real estate business, according to the last IRS info I saw, you cannot deduct improvements or upgrades.  

Then you can work on improving them.

Hi, I know a company that can improve your capital with a credit card.