Tax planning is a long term game and if your advisor had planned your investment and potential disposal, you could have mitigated some of the taxes. 

Flipping would increase your taxes because you have new self-employment taxes to pay, if you didn't use some tax mitigation strategy.Big picture observation: your taxes shouldn’t have increased just because you bought these rentals (unless these rentals gave you huge positive cash flow even after depreciation during the first year). 

It is the difference between your adjust cost basis (acquisition +improvements-depreciation) and the net sales price.Your choices for tax mitigation on the sale while staying an investor would be a 1031 exchange. 

The fears you mention are lower, reflexive fears that can be mitigated and overcome with education and experience.If we focused on all the what-if lower fears possible, we would never drive.

New paint, flooring, new kitchen remodel, complete basement refinish, complete landscaping refinish,structural reinforced and water mitigation added What was the outcome?

Mitigate, yes, eliminate, no. 

So if your going for an SFR as opposed to a multi unit.. if you buy at those price points you will break even or maybe be 100 to the good maybe 100 to feed it.. but you will mitigate the RISK hugely. 

Is the school growing fast enough to mitigate this?

Rates have bumped up slightly over the past month so you're likely in the 4s no matter what at this point on a pure investment property (not primary residence), but big picture still a great time to use leverage with historically low rates, and to mitigate your exposure to the crazy amounts of inflation we are going to see over the next few years. 

Assess your situations and scenarios, come up with ways to mitigate or eliminate the threats to your business or personal assets, then put a plan around it.