Naturally that will make a difference as well. 

I will say this group is national (even some international) in nature and is not the best for resource for finding local data especially in niche markets. 

And of course it has worked incredibly well on the money raising side.. what I see happening is a very natural progression with someone who has the visibility and popularity as Brandon.. it takes a huge support staff and fulfillment team to create what we are seeing.I think you are on to something.I think Brandon's role is not necessarily to find the deal or to manage the deal.

Welcome to BiggerPockets, Tyler — your background in engineering and hands-on property work makes the BRRRR strategy a natural fit for you.

I really enjoyed the process and realized that I have a natural ability to connect with people over the phone and break through some of the usual resistance that comes with cold calling. 

Even if the property or contract were technically held for over a year, it would still likely be taxed at ordinary income rates because the nature and intent of the activity look a lot like dealer activity (i.e., flipping or developing with the intent to sell).As Josh explains, the IRS and courts tend to focus heavily on intent and the taxpayer’s ordinary course of business.

(I have experience raising money as a professional musician so this came somewhat naturally to me). 

However, that's less than ideal for me because it automates 2 separate templates (one isn't customized and explained above) and the other is VRBO's email template (which I can't find yet to edit or get rid of) which has all sorts of incorrect things such as review the rental agreement (we don't have one beyond House Rules) and how to pick up keys (we're 100% smart locks).You're exactly right with the clunky nature of high demand dates so in one case when I actually pre-approved a return client, they couldn't pay (that was the problem and absolutely with VRBO's system) despite repeated tries and another request from a different guest for those same dates overrode my pre-approval and it was a huge mess.As hosts, we have to act as if VRBO won't find a fix.

I'm ignoring any and all appreciation in my analysis (natural or forced).The biggest challenge I'm noticing is my entry point and available cash on hand.

I will receive cash flow based on my exchange amount (4.2M) + my TOTAL reserve amount even though I have not yet contributed that total reserve amount.The sponsor/manager is confident that the amount in the reserve fund will be adequate (he says more than adequate) and that there will not be a need later for additional funding.