This is just a baseline and understand the value of good software but do not see us having 50 units in 5 years since we only self-manage. 

Note self managing will impact the ability to scale.  

I self manage 29 SFR and it’s easy. 10 are out of state so it’s doable for anyone.

My advise is to start with single family or a small multi-family ground up project first but this market environment is truthfully not the time to be completing any ground up projects unless you are self performing the construction which it doesn't appear you are in a position to do.There was a recent Philadelphia  forum chain started by someone else who was contemplating ground up in a similar fashion to what you are proposing and I cautioned they would be better off buying something that was newly built and believe after conducting their own diligence realized it was too cost prohibitive at this time to build with 3rd party GC's in Philadelphia when also accounting for the interest rate environment and cost to build.

Insurance will require a self closing gate, but the guests will always prop that open. 

Should be very similar to Self Storage.1. 

The one difference with Josh in this area is teaching you how to self direct IRA's and what to have in place so you can do it legally.

I also self-manage.

Has anyone had experience taking over a self storage business and raising rates $5-20 per month?

I'll just self-insure for that risk.We manage about 30 properties in total, and usually have 1 BB case per year.