If you think its a deal, the wholesaler also does flips, so why is he not choosing to do this flip?

I provide live videos for my out of area (usually CA or east cost) investors, and many of them choose to purchase without making the trip- and many of these are $800k-$2M purchases in Sedona.I have a similar story to yours, from when I started investing 25 years ago.

You don't really "choose" which method to use. 

I keep trying to post on the Marketplace forum and I get an error staying I need to choose the post type or something like that.

Then ask how many vacant units there are to choose from.

Second is to make sure you’re in a position to close if they choose to sell their property.

Now I get a feeling of accomplishment when 80-90% of our tenants choose to renew their leases, and when they ask on behalf of friends and family if we have available units - we must be doing something right!  

If this was a long time ago, (whatever that means) the title company may choose to insure the title anyway.

Assuming you have cash-flow and build reserves for EACH property I'd choose the higher deductible every time (unless the property has lots of deferred maintenance).

@Tal C.Number one I would say is to choose your target markets, neighborhoods and then put together your team on the ground before starting to look at any properties.