It's pretty convenient, although their coverage rates are relatively high and you have no say as to what coverage you want.

You can start here:https://www.biggerpockets.com/real-estate-investin...Also you should start listening to podcast, it is convenient you can listen in the car, in the gym, etc. and will learn a lot! 

Aside from realtors, you could always prospect yourself which I find so much more convenient with condos.

I do the walk through either the first day of the lease or a day or two before if it is more convenient.3.

I didn't start out planning to become a landlord, it was just convenient due to a personal medical situation.After everything cleared up I formulated a plan to jump in to the industry so that I could retire early.

Bryan,Here are the 3 main options to consider:1) Custodial self-directed IRA, lower upfront cost but watch out for transaction and asset based fees, have to go through custodian for every transaction, might be inconvenient for certain investments. 2) Checkbook IRA (aka Checkbook IRA), eliminate transaction fees, higher upfront cost because of special purpose LLC, but long term will provide savings and most importantly a convenience of having checkbook control over your retirement assets. 3) Truly self-directed Solo 401k, requires self-employment activity or small business, the best option if you qualify.

Potentially thinking of house hacking near my job for the sake of convenience for investing and working!

You could allow them to drop their payments in the night deposit along with the proper deposit slips provided you trust them not to make mistakes on the deposit slips for which account and who they are making the deposit, however; if you want true 24-hour convenience to a few tenants, get them an employee, deposit only, card for the ATM. 

It's an excellent lifestyle...lots to do but it's convenient and still affordable. 

(and this is all even before taking into account all the returned letters you're dealing with currently sending out 500/mth) ; The convenience of sending a list to another company to handle all the outbound letters, far outweighs the extra added expense.