Almost no repairs were requested.

No one on this forum will be able to answer his question unless he wants to provide his income tax information.Capital gains at the federal level is either 0%, 15% or 20%.He may have capital gain carryoversIt may potentially be considered a business and subject to ordinary income which would be at his marginal tax rates.No one knows where the flip is done or in what state which impacts his state income exposure.

I really had no idea people could act like this.

But, if someone does the same thing as everyone else, and expects different results, would it be unreasonable to call that crazy...? 

The best thing about this is it's a free source for building connections and getting information on local meetings.I have found that no one source will give you all the helpful information you'll need to be successful.

Just getting some "dirt" as I like to call it is the first step, the amount you will learn by jumping in and just buying something will teach you volumes. 

You should also involve Vrbo if something comes up that is beyond your control.I personally have never had to cancel a booking, so I don't see this as a big deal.This must be an issue for them to come up with these rules.Preparation H has a warning that says no to take orally, probably because someone did do this, so they had to create the warning.  

In my case, I always tell prospective tenants ahead of time to expect an email from this site, and so far (knocking on wood) no one complained.

No LTO contracts.

Quote from @Mark Prather: I continue to get emails from Steve Mayer of Finance holding Company, but he keeps wanting me to pay a deposit + his 2% origination fee upfront...seems like a scam and wanted to see if anyone has done business with them in the pastI don't know Steve Mayer of Finance holding Company.I do know that no lender should be asking you for an origination fee until they ... actually originate a loan!