My immediate question is on changing PM software. 

their bookkeeping software leaves a bit to be desired though, i always have trouble connecting my bank accts so i just manually upload the file monthly now. i'll live. i like how simple it is. with RR tenants can pay through the app, they get reminders, you can manually send reminders, they can make partial payments throughout the month, you can pay $5/unit to have their on-time payments reported to the credit bureau to help build their credit, you can do apps and background/credit/eviction report on there.. and yeah in MA there are just so many stipulations around how security deposits can be used i'd rather just not even deal with it. 

Not a CPA or tax professional.I’ve never audited every single line item of my S-Corp tax returns for over 18 years, and I’m truly curious why it really matters in one years instance, what corporate account was used to conduct business, as long as the financial information is accurate and correctly reported from said dedicated business account.This should be a separate issue from proper and legally correct business operations, ie a checking account with correct tax ID, no outside commingling of funds with self or other business entity.

Does anyone know of any software that people use with co-owned properties to manage shared use / access / time, etc?

Definitely plug your property into a pricing software and educate yourself on how to use it.

There is plenty of office support, AppFolio software, I am open to bumps in commission/bonus structure -- portion of rent raises, lock changes, identifying more MF buildings, commissions IF we decide to sell any properties, etc. 

The software has been super easy to use and great for self management.  

I got audited for 3 years. all of the above was thrown out.One example I had a business trip to London then to Tel Aviv. 

If the two of you were simply individuals owning the property as tenants in common and neither of you owned more than 50% of the entity then you could make the case that it was not a related party transaction.My fear is that if audited the exchange would fail due to the closeness of the related transaction. 

@Patrick Fanning - I think the advise you have gotten so far is pretty good (I'd recommend getting an energy audit from energizeCT).