Per his lease (and common sense), he should cover the cost of repairs to my unit and the unit below, but I have a lot of questions that hopefully the veterans here could help with...1) Does my homeowners insurance need to be involved at all?

The number one thing I would suggest is to get involved in local real estate meetups and start to meet other wholesalers in person that you can develop relationships with. 

As far as I know, self management will probably be your best bet as the property management companies in the area are not fully matured.

That's wonderful, are you involved in any meetups in the metro area? 

Per his lease (and common sense), he should cover the cost of repairs to my unit and the unit below, but I have a lot of questions that hopefully the veterans here could help with...1) Does my homeowners insurance need to be involved at all?

In her personal life, she is involved with someone who deals drugs, as they do drugs and are involved in illegal activities.

Quote from @Dan Ikon: World Cup is huge - it's even bigger than Olympics, and Miami is one of the host cities.I was involved in accommodation rentals in previous cups - in Moscow, and before that in Germany.

Youre best bet is to partner with someone local to you who is experienced and can guide you along the path with this.

And if you can't to conventional for some reason, the DSCR loan is probably your next best bet. 

I bet that's a picture the younger Canadians see, what could be.