This opportunity has allowed me to not only gain great knowledge about parking, but commercial real estate as a whole.

Also less risky - the gains may not be as high but the losses also shouldn't be as bad if things go south. 

You have areas where property taxes are going up too fast based on the over valuation of properties  ( tax on unrealized gain ) .

I'd do a 1031 exchange and defer capital gains.

Is it better to use "involuntary conversion provisions to take a deferral of the gain on the loss of the previous roof assets and continuing depreciating the prior assets as is"?

This is not a "real estate rental income" activity as defined by the IRS, so whether you are a REP or not, you can take this benefit.All of this is separate from a QOZ Investment, which would require you to first recognize a capital gain from another source (say a stock sale), invest that gain, hold it in a Corporate or Partnership structure (likely partnership), meeting the substantial improvement qualifications of being a QOZB, and then yes, you get to avoid the depreciation recapture at the end of the 10 year hold period, at least for the portion of your investment attributable to the original gain that you invested in the project. 

You will have earned $90,000 in rent income and gained $34,000 in appreciation after five years.or...Buy four houses with $50,000 down on each.

I thought this was strange, and they commented they wanted to buy it because they had a large gain and wanted to buy it to offset these gains.This was an immediate red flag.

Everyday that the property is vacant you lose money that can never be gained back.

This is a fantastic place to gain some insight into the REI world, particularly for those starting out.