Bill and Abby,I am on the Vos Team @ Atlas Real Estate Group and we specialize in assisting investors find the right income property.  

If not, just partner with a good real estate agent as a part of your REI team.

Once we sell should I venture out on my own or try to get my brother to invest his half on the next property together as a team?

We specialize in not only property management but we also have an excellent association management team also.

Any software you use, needs accuracy, booking, consistency, dedication, education, reporting, analyzing and more.

Any advice is greatly appreciated.David,Here's what I do for my multi-family buyers:Yes it is hard to estimate for maintenance because of a lot of variablesBut I know its expense is less for more units, for things like 16+ unit buildings, onsite maintenance room for storage materials, onsite employees use less hours to do work ordersSome entities even volunteer their residents to pick up grounds, hence minimizing your maintenance costsIf hdsupply.com accepts your account they specialize in multi-family buildings and you don't have to use man power for delivery or pickups And yes, you can do analysis paralysis but it might help you the bank's formula DCRThe 1031 buyers look at expenses differently Yes there's a number per door, e.g. if the units have been neglected you will spend at least one month's rent in turn ready unit expense    An organized well lubricated team should turn ready units in 2-3 daysPay close attention to the human factor, i.e. low self-esteem employees who will take longer to turn ready units or do work orders with poorly workmanship, theft, etc In capital expenses, concentrate in a few and more expensive to start with, AC, plumbing, electrical

Basically, you have to be buying in an area that is NOT predominately rentals if you want your property to appreciate.If you want appreciation, get yourself a professional, local team.  

In addition to my personal real estate investment activities,  I currently work part time with a 501(c)(3) non profit dedicated to helping inner city youth.

It is a good way to grow your team and your knowledge at the same time.  

Refine your goal and determine who you want on your team.