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

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.

Affordability will naturally go back down.1.  

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.

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.

I always add things if this nature under the additional clauses section of the lease.

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.

No need for that in any kind of business, especially Real Estate.Some people just naturally run on fear and negativity.....realize this and treat them kindly.

Out-of-state investing has its own risks: travel time, reliance on contractors/managers, and the need for cash reserves if something goes wrong.It’s natural to feel like you need to “start now” or you’ll miss out, but it’s worth weighing the pros and cons of buying a $125K property in an unfamiliar market versus leveraging your capital in an area you know and trust.You’ll see plenty of posts about Ohio or other markets being “the best” due to jobs, affordability, and population trends—and there is money to be made in many markets.

If you prefer things to stay more passive, you might be better off keeping the current setup or looking for another property that naturally cash flows higher.