You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

How will his syndication deals work out for his investors when he is forced to refinance at whatever ballon payments he financed the deals for?

One cannot control the outside forces (government/economy/career/medical/etc.). 

Same with putting a larger deposit down to make your monthly payments lower doesn't mean you are cash flowing more as you put more money down to 'force' the cash flow.What matters most is that you are happy with the numbers and they work for you.

We used Verivest and recently were forced to switch fund admins by our bank and switched to NAV.

Don't force the next opportunity. 

I would rather spend some front end money now and do a relocation, then be able to use simple side-by-side units than to be forced into stackables or all-in-ones.

It may be easier to offer the Tenant $6,000 to leave and be done with it.Unfortunately, many bad tenants have no fear of the legal system and they will continue to abuse this until you are run dry or the court finally forces them out.

*********************IMO - a deal should not be forced into your "buy box" because you are overly motivated for any reason.

Tough to do that in the stock market and pretty rare to do as a performer/athlete, like 1% of the 1%, and for C-Suite again have to not only probably be good, but lucky to be in the right place, at the right time, at the right company, with the right opportunity.