Something I found odd is the calculator's projected cash flow seems to improve over time.

Since taking possession of the property, we have made significant upgrades to the property and improving the value of the property and making the building more aesthetically appealing to the neighborhood.

It's not a total piece of crap, but it certainly has a lot of room to improve the value given the market that it is in.

I have been using it for a year now and the software is improving.

I'm still doing improvements all these years later (bought in late-2016) but the value-add reality and rent bumps is as real as it is wonderful. 

Then, if you do an analysis after 2-3 years projected cash flows stabilize, equity improves, and the area is growing and we’re seeing larger national businesses move in, so I think the growth trend should continue.

But I don't know with those improvements if we could have gotten it up to 425. the as is CMA my realtor did on the property came up to 339,000. and it was listed at 315, I'm interested to see what the bids were on the property.

Trying to meet and exceed expectations isn't easy, that's why we NEVER stop improving:)

I’d do the improvement.

We keep track of property expenses - all maintenance expenses, improvements, and business expenses, as allowed in the tax code (like a subscription to Wall Street Journal and lunch with other investors).