If you need more to do the rehab, perhaps instead of partnering, you could get your former boss to do a personal loan. 

A nice but expensive duplex on a beach or in an expensive area might be ideal, if you can swing the other half out of personal funds. 

There are legal requirements for disposing personal property left behind by a tenant.

I personally use Hostfully and their support team is great!

@Antoine Black  In general, yes, it goes off your personal credit. 

Shadow/mentor a person doing it.

There's no clear-cut answer IMO, it's a personal decision.  

I have sold some properties years ago on lease options where the tenant buyers actually exercise their right and purchased the property. ( I was in the deed.)The reason I am concerned to tie another person’s property up  with the lease option is that people can change their mind, as in the seller.  

Personally, I find BTRs to be more predictable with fewer ongoing maintenance issues, and they tend to attract high-quality tenants.

Sometimes you will have that next person/family lined up and ready to go, but sometimes it takes much longer and you need do renovations or at least some repairs.