A good realtor can be a great asset and definitely be worth the cost in commissions, but bad ones can potentially crush profits.

Moreover, in the software community, "hacking" is not black hat activity at all; it's simply the job of putting software components together to build something useful. 

As well as that side of due diligence, I reckon your greatest asset will be: having the right Property Manager.

If land lording is in your long term plan no sense in selling off your 1st asset that likely has a more favorable owner occupied loan on it to later buy another property with a less favorable loan.

@Hans H. when you say you send them an application what kind of software do you use for that?

They are a team of attorneys and CPAs who specialize in asset protection and tax savings and they work primarily with real estate investors. 

Just curious what software/tech people usually use to streamline that. 

Hey Guys -What are some of the pain points you experience when using property management software?

Some of our clients are good with software and invest in private software ventures.

Who they are using for tax accounting, property management, general contractor if any, mortgage broker, due diligence company, cost seg, insurance company, and etc.Review the additional fees\costs, if any, and determine if they are out of the norm depending on the experience of the sponsorship team, investment strategy, and asset.