How did you all go about learning these concepts well enough to be comfortable taking that leap?

Be careful about those Items being "free" is usually raising a red flag. 

You quickly learn which ones want to talk for ever and which ones just have something quick to say.If it is important or a real problem I can call them back.If it is a repair issue I then text my handyman or HVAC guy to go fix the issue and it only takes me a couple minutes to deal with a issue.I then follow up with the repair person to make sure things are taken care of.

They take care of a few malls in Northern NJ and I used them to do a part of the parking lot at my job.

Might help put the concept into perspective?

I want to be careful. that being said...Have any of you encountered this and made the decision to take a building out of your LLC to qualify for this better financing?

Of course, if you hire a property management company to take care of this for you they often have tools and processes that are built for these situations.

Hi I currently run a property management company and one of the services we offer is we take care of buying tenants out in Los Angeles we have a few guys that do it for us but they are always really busy with other properties as well and as we grow our portfolio we need more people to do buyouts for us If anyone here can recommend someone that does buyouts in Los Angeles I would greatly appreciate it p.s Sorry if it's not being posted in the right thread I am new to bigger pockets

Second, once you issue 1099 what do you care what he does, you've done your part.

This time I would let others take care of both.