How do you balance these strategies, and what signals do you look for in deciding to hold or flip a property?

Another time my Buyer decided to wait the two years to get her earnest money back. some markets  like SC its common for the broker to have a trust account .. most others though EM is handled by title or attorney. 

@Ed Lopez what controls do you have over what they decide to do?

We are purchasing and rehabbing a short term rental, but need to decide whether to put  in our names or in an LLC?

Quote from @Dan Zambrano: Hey all,After thinking it over I decided to create a new thread.I am a small time passive real estate investor who has ambitions to expand greatly, first to $20M and perhaps maybe more. i guess I will give a little bit of background on my journey up to now.I am 38 y/o, Electrical Engineer by day, Architectural enthusiast by night.

Other than new construction development same here we have no senior debt its all cash.. of course unlevered returns are are a little less but man is it so much easier to manage and not worry about paying the senior debt all the reporting One has to do etc etc.. having been through a terrible down cycle with syndication decades past and watching what the guys I worked for went through and lost I just decided if we cant pay cash I am not going to do it. 

However, the escrow servicer reneged on the options at the last moment and decided they would only reimburse a HELOC.

I'm deciding how long I should hold onto those properties and if the Class C will appreciate enough.

Like you, we decided to look for a property in the RRG because we like to go there.

But once you declare to be running a trade or business - then 1099s do come with the territory.If you really want to avoid 1099s and decide to claim to NOT be running a trade or business - be prepared to lose your business overhead deductions upon an IRS audit.