The software system we use is Propertyware but I know other systems like Appfolio have account keeping.  

Sellers and sellers agents knowing your agent is the real deal, represents real buyers, has great business systems in place and has done the analysis to justify the offer is the total package of negotiating.  

The time it takes to get through the court system I find it may be less expensive. 

Forget what your "goals" are, it's all about the decisions you make and systems you have in place.

All major systems have been well maintained. 

As for ease of switching over, it really all depends on how organized your current data and business systems and processes are.

They know the tenant base, median rents of different areas, how much to increase rent each year, ranges of repair costs (ex: tenant calls and says AC isn't working, no hot water, faucet is leaking, the HVAC system goes out).

How would you suggest I handle an expense like let's say new HVAC system is needed a month or so after we close the deal on the portfolio?

@Allen Moore In New York City, section 8 is awful, the tenants play the system masterfully and the courts are in bed with the city.

That layout is fairly final.Luckily not in a hurry and just work the system and not get in a hurry.