Just to cover yourself,  find other non-discriminatory means to decline them like credit score, criminal background and eviction history.

Meaning you buy a multi-unit, like a 2 family house and you rent one part out to tenants and the other half you live in it for about a year or two before you move out and find other properties.House-hacking pretty much covers the 2 options you had stated. 1.

This leads to frequent move-outs and escalating costs of ownership.  5% for maintenance and 5% for vacancy do not even come close to covering these costs.When companies are competing to see who can race to the bottom first (lowering prices and selling property cheaper and cheaper) they have to cut somewhere in order to make a profit.  

This application covered most things - but I'm wondering if there's anything that was left out of if it's asking for too much information (i.e. credit card information / balances).

file for lost rent and additional damage if any not covered by damage deposit.

Since I'm paying cash and will have no mortgages, sounds like about 6-9 months gross rent should cover it, I guess.

Can it cover Multiple properties and does it come a lot cheaper than having Landloard Insurance (Covering Fire, hazards, Wind... ) ?

The pitch sounds good: I can rent out some vacant land for camp spots with essentially no improvements, and they cover the rest, and I keep 90% of the revenue.

That may only cover your original loan. 

I usually just install a CO/smoke combo on all floors while making sure they sleeping area one(s) cover all and that works just fine with the inspectors.