It sounds like you should start looking for a PM that more aligns with your processes.

Leases typically run August-July to align with the school semester.

It's really best for apartment requests over ~$3mm with little mixed-use components.

Deferred maintenance I think of as things that need to be done that don't really provide a value add component and wouldn't command increased rent or help reduce operating expenses.

Neither has happened.In most parts of the country, there is a huge shortage of inventory due to the fact that the labor component of construction left after the last downturn and have yet to return.

As for the building components, look out for undersized floor joists and beams, along with no footings.

I just rent my 22 STRs to travelling contractors working short term jobs at a petrochemical refinery and its ancillary components. 

They often get stuck and you have to stand there wiggling it a lot and re-checking alignment. 

The company he invests with could be of low quality (present company excluded, LOL), could lack a track record, not have experience with having survived a market cycle, could produce inadequate reports that don't tell him what he needs to know...whatever it is, when investing in a syndicated offering there is an additional risk component that isn't present when buying real estate directly--the sponsor of the investment.As an investor in a syndicated offering you can't typically 1031 exchange in or out, which you can do when buying real estate yourself. 

Make sure your brother sees/hears/ that your mother is in complete alignment with this timeline.