@Luke Bricca Yesss...my heart is really in renovating and giving houses a new life (did that with my own house pretty much) but alas I live in the Bay Area so there is nothing I can afford here....or anywhere nearby really... plus a small kid (so travel is hard), so hard to travel frequently and supervise a contractor, etc. 

Lower end tenants mean more headache:More frequent turn overHeavier turn costs/higher wear and tearSlow paymentsLonger vacancy between both the turn over time and finding another qualified tenantBeyond these factors, as others noted, a full unit renovation will cost about 15-20k if you want to do it pretty nice.  

I am normally a fan of self-managing and building a team, but it seems you ran into some issues there.

Not many people actually care for Hostaway, but there's a few major fans.

Frequently the price is higher than a consumer would get if they contracted directly with a contractor.  

I post on here frequently.

I'm not a huge fan of the current pricing structure--which is a different issue--and we often don't use a buyers broker but it is far easier dealing with a seller's agent then the seller.

Vrbo says they also give preference to listings that are updated frequently. 

So I'm a fan.

I've tried everything and done everything "right" according to what everyone says (professional photos, changing rates, premier host, updating listing frequently)...well this was a surprise..."