But like I said, perhaps my folly is simply ignorance into crypto mechanics. 

You can have a PMS like Hospitable with custom auto messages and AI assistance to answer.

My A class that I own I self manage I have a RE agent that puts them up they find a tenant I require 700 plus fico so that weeds out 90% of renters and then I set them up on auto pay and if they have an issue we send handyman.. to be fair my units are basically new construction and townhouses in HOA's in the Desert ( vegas) so there simply is not a lot of maintenance. there is A class in every city its just that investors get so focused on  positive cash flow they dont buy those for rental purposes so they miss out on the best rental tenants.. the higher the cash flow on paper the lower the quality of the units.. its a fact..

That is what auto insurance is for.

That same night I set up auto pay.  

Their auto-categorization is also rock-solid. 

So, you propose selling that and putting it into a two-family where you get twice the mechanicals and your first handling of renters.

I have $30 k in savings, no auto or student loans and excellent credit.

They will love seeing the owner explain things before they arrive.Send auto messages the evening they check in and ask how things are going to get ahead of any problems. 

I think, for now, I’ll probably use Buildium (my current software) and manually enter into furnished finder and AirBnB and require approval so it doesn’t auto schedule and so I can send a proper lease.