The people in the room are the people you do business with they have the deals, the money, the services, the knowledge, the legal help and everything else you need to do a deal.You could try to make those connections here on BP, but nothing beats going to a meeting and talking live and face to face - you might event get to meet Andrew, he speaks from time to time - or all those vendors - we had 40 of them in a room last month just for everyone to come ask them questions.So find your local group - where ever it is - find or join several. 

There is no risk that you have a guest in there for an extended stay who decides to complain about something and Airbnb refunds part or all of their payment and there's nothing you can do about it.

I know you said all in or all out, but what about getting a full service property manager so you don't have all the headaches of being a landlord?

But you can also loose some or all of your money if you do not perform your due diligence and watch your investment closely.Happy investing.

made an offer on a property only to find out later that one of the units was going through an eviction.tried to extend our inspection contingency to no avail to buy us some timeended up not being able to come to terms on how to proceed with sellerthe last HOUR of our inspection contingency the seller offers to try and buy out (cash for keys) the tenant the next day (he had a property manager handling the eviction and wasn't even aware of it initially).i get a (risky) oral agreement that even though the contingency window had passed, if the plan falls through my client will still get their EMD back the next day the seller ends up buying out the tenant for a bit over $3,000 and now we can move forward with the deal without the headache of a problem teanant/ picking up an eviction.

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.  

If not then one or all of them need to go. 

I you could buy a duplex or 4 plex you could have most or all of your mortgage covered by your tenants and begin save money for further investments once your son is out of school. 

You can use part or all of that bucket for a house.

Given your numbers, it seems this may offset most or all of your tax liability and make it easier for you to utilize a new entity structure.