We'd like to combine our 401(k)s into (hopefully one) self-directed fund.

I'm a little confused why this would be a fit for someone just starting with note investing, vs getting into the diligence and some of these platforms like paperstac, etc oneself?

I have heard all the stories about terrible wholesalers, but as a person that loves to study I can see the potential wholesaling possesses when fully educating oneself on what it takes to be an exceptional wholesaler.

However by educating oneself on the subject matter and obtaining mentorship than it can assist with avoiding major mistakes.

Surrounding oneself with the best kind of people is probably the best "high level" decisions I ever made. 

Truly, safety and security of oneself and belongings are paramount, and I won't begrudge a neighborhood from installing a gated fence, nor measures to encourage (not force) character/architecture retainment, but again, I have yet to see any data that support increases in crime or poor performance due to the presence of STRs - more importantly, then, is ensuring the city/municpality is afforded the oppportunity to welcome in visitors; Businesses thrive, jobs are created, demand for the area and its amenities increases, and values rise, which is something ALL investors want. 

I've only evaluated one self storage deal, in a 3rd-tier market with only one other true competitor.

I'm sure not one self-storage developer in those markets projected a 5% to 9% rent DECREASE in their lease-up pro forma.

All the other items you list can be obtained either oneself by making calls to the various gov't levels and utility companies.

I personally think the HOA can help one self manage by taking care of things like the exterior and common areas.