I've looked at all of the large RE companies such as Keller Williams and eXp, but I want to do this part time for now and keep my current job until I'm comfortable enough to leave.

He is VERY real estate friendly having owned several of his own properties and handling several of us who have larger portfolios. 

The main things about renting to a group of inexperienced tenants is that they may not take timely rent payment seriously, they may not know the housekeeping tasks necessary to keep the rental clean, they may not know when to call about minor maintenance issues that can grow into bigger problems.  

Potentially selling and making a $100K to then buy a larger investment would be the plan but then again we could utilize a 1031 exchange if the timing is right later down the line. 

Hiring someone in a real estate business could include a thousand different tasks and what they are doing makes a difference in how the question is answered. 

A friend of mine had an idea to buy "smaller cell sites" since the larger towers seem to be out of our price range as well as dominated by larger players.

I'm sure eventually I will outsource this task, when my investing career in much further along. 

All else being equal, a smaller unit will sell for a higher amount per sq fit than a larger unit.

I would feel very comfortable if I had $7,500 reserved owning a duplex incase I ran into a major maintenance issue or larger unit turn. 

Hopefully earning equity on the rehabs along the way, so I would be using a smaller and smaller portion of the heloc over time(or being able to go for larger duplex/multi fam properties)...Does this make sense?