Having someone on-site who is doing snow removal and lawn care is excellent, in your case, you have to ask, is it worth a concession or is it cheaper to hire someone to perform a professional service - it gets tricky when your tenants are also completing property tasks. 

Some agents would possibly pass that task off to an assistant or you may very well find an agent who would do them for you.

You can trust others for some tasks but really!

He requires contractors itemize every single job and how much each task will take.

I qualified based on personal experience which means buying, selling, renting, mortgaging, etc. of my own Properties.I opened my Firm and will probably purchase a property sometime this year in the $2 Million range which should give me a 3% Commission or around $60k.HOWEVER, I am also thinking that I would like to offer friends and family my service as well and to give them a discount on my commission... at least in the beginning few years until I really understand all the things a Broker really needs to know.I'll probably just concentrate on being a Buyer Broker rather than listing as I don't have experience YET at selling.I won't take on an Agent just yet either until I fully learn all the normal operations of a Residential Brokerage Firm.The dilemma I am having is that because I have not worked as an Agent, I am now tasked with understanding how to run a Brokerage firm from scratch.So even simple things are unfamiliar to me including:1) Associating/Disassociating Agents.

Also if you have no experience in real estate taking in a 16 unit building is an overwhelming task and if you do not have a good PM then you lose it all very quickly.

Don't expect to get paid in this scenario and expect to work awhile with them to prove your worth BUT you are actually doing tasks specifically related to the real estate deals with this investor.

No, not sure of that @Samantha ViceHowever we have had some mixed success with using Trello which is kind of a scrum/task management kind of platform.It would theoretically work but you need to build in enough process and get buy in from your team otherwise like anything else it just doesn't get used.

I'm going to start keeping an account of my adventures here. 

Your right I need to find one thing to focus on and stick to that and once that’s done move to the next task.