The first and biggest problem is that all lenders that I know of will only lend on a transaction that is arm's length, meaning not being purchased from a family member.

My biggest struggle is that I am OCD about timelines and communication....dealing with lenders, escrow officers, other brokers and sometimes clients that ignore timelines and communications brings me a lot of daily frustration.

This is the biggest investment of my life and I feel like I should be making a more educated decision rather than just picking the first person whom happened to have a listing I was interested in.  

The biggest pro is that I won't have to involve my mom in any way.

The biggest difference I can find having been on both sides of this is simple marketing -- Realtors can use the Realtor logo, receive created Realtor designations if they pay more to take association classes, which they can use to promote themselves (more marketing like the logo), and may benefit from the Realtor commercials promoting their membership. 

Only downside is the delay in the deposit (4-5 business days) but that's a fair trade off IMO.

The biggest perk of having a license is access.

Only downside to this method is it's messy and dusty, and if you ever have to patch the ceiling matching the texture is really difficult.

We're open to both long term rental tenants and short term using Air B&B for example.The kids will be enrolled in North Port which is the only reason we dont purchase in Tampa which shows to have a great market, so trying to stay within 30 minutes travel time from North Port area.My biggest problem is paying rent for about a year, when we can just as easily put it towards a mortgage if there is an area that makes sense close by long term.

You'll have to pay the local Board of Realtors to gain access to the Multilisting Service (your biggest fee).