He sounds like someone who's just an idiot, getting in trouble all the time while dad keeps bailing him out - a pretty common scenario. 

Look at the condo docs to ensure there are no limits on rentals, how it is run and the financials.Pros of a condo include lower property tax than a single family, you don't need to maintain the common areas and there is generally a lower price to entry.Cons if you have a poorly run condo, it can cost you; the condo/HOA fees add up quickly and you can often put that towards mortgage payments and get a single family house, if you have problem tenants, you have problems with neighbours and possible fines.

Perhaps not a common practice but there were my eyes and ears and I trusted their judgement to handle and manage accordingly.

As far as ownership, most lenders want to see at least 3 months, 6 months is the best/most common requirement, some require 12 months.

@Vincent PlantThe 6 month seasoning is common knowledge and there are a number of posts discussing the  seasoning period.  

Below are the questions I'm seeking answers to:1) Are there certain types of cases that most policies don't cover but lawsuits  related to them are fairly common?

The operating cost includes: tax, insurance, and HOA (covers exterior maint, roof/foundation, lawn care, and all common areas).

Multis / rentals are not common, and in demand.

Will depend on the seller but I think there should be a way to come up with some fee for common area maintenance and rest taken up by me.

It’s just common sense to think that the risk gets bigger the farther away it is from you.