Vacasa has AMAZING marketing & online technology but ZERO ability to handle operations in this market. 

What is the most efficient way to have your tenants pay their rent using today's technology? 

So yes, it can be done especially with some of the technology, tools & systems in place that the other BP members have suggested.There are sevaral ways one can go about handling the management of a vacation rental property.

To this day, the only things I outsource are some technology support and social media/marketing related tasks. 

It seems like technology nowadays should be able to solve this one.

I think there's a real sweet spot there that lies between small multifamily (under 4 units) and the larger commercial properties (80+ units) AND a danger zone in there.

Technology and market disruptors are a major driving force of the deflation we've seen.

We regularly meet with potential venture capital investors in our co-working space, but that's the expectation for technology startups.From our perspective, we can't afford the "chains" associated with a long-term office lease and would rather pay more  "per square foot" to retain the flexibility to grow or contract quickly.

Based on your post, would you say that the possibilities are either a) he really is broke and his "I just dont pay myself" isn't accurate, or b) he's lying to the IRS?

You got to be careful here.I sense your tenants may be up to no good.6 months ago,I found myself in similar situation with a tenant that had a similar MO.Like in your case they complained about everything in the newly rehabbed home.But I quickly realized all they were trying to do is to justify no paying rent by claiming they are withholding rent for deferred  maintenance  that I failed to do.They lied  about the water heater was broke and got an estimate to replace from a dubious handyman.Water heater still works till date.Long story short,after the rent was late a second time,I stopped taking rent and evicted them.I later realized they have been doing this for a while to several landlords and apartment complexes.Always screen your potential tenants,mine wasn't properly screened.