Vacancy reports and Development forecasts were also part of their benefit of services.Unfortunately, they decided to retire in January and closed shop.

If you are asking if one strategy is riskier than the other then  the answer is mine is but thats only because of diversification alone.I think what you are asking is  what is the  riskier strategy. the only time my strategy would benefit me and hurt him is if the banks start having problems. for example if the bank calls the loan due for some strange reason he would be in trouble as opposed to me where I dont have a lender. 

The two things that Derek said are safety essentials in any Lease transaction. 

But you're total gain including depreciation recapture was $60K so you would end up having to pay the tax on all $60K - no benefit to the 1031.The other question you're hinting at is what if you bought a tract of agricultural or hunting/fishing land that you intended to use for productive use (wilderness activities, rental, agricultural, livestock etc etc). 

I can see a benefit from not having to re-key a property and offering the smart home system as an incentive for new tenants, has anyone thought of this for their duplexes or multi family units? 

Some will argue that by paying down your debt, you are losing on the benefits of leverage.

After a little reading here and there, I figured my best plan is to save up while I'm in college and then buy a 2-3 flat, live in one apartment, and rent out the rest so my tenants essentially pay the mortgage.

The benefit to the seller, is that they save on commission... so they should at least cut a bit of that off the price, right? 

Essentially it reads that they reimburse me for water/sewer/gas within 30 days of bill receipt.

You did not point out a big benefit.