I live in San Diego, CA and as you all know, it’s a very high entry point here so looking to get into a long term rental elsewhere.

That one and a duplex off market sitting right next to it are right at the edge of a B neighborhood and going into a B-/C+.

Condos are cheaper than houses, and to my mind, a vacationer wouldn't care much about staying in a bigger place for their short stay, and would be more concerned with a good location and a nice view.Thoughts?

We use Turbotenant and used Apartments for years before that and a different one before that, that apartments bought out.

I don't love the idea of having prepayment fees and a mortgage on my free and clear property but if I do a combination of things I would be able to make an above garage apartment at house 3 for 15k-20k that rents out for $1100-$1300.

If you have a solid ARV AND a great GC / team that you trust to do good work, consistently, and can stick to the timeline planned, even with hard money you will still make money at 75 or 80%, albeit a little less than at 70%. 

Also, monitoring contractors/sub contractors and keeping everything on schedule can be very difficult remotely.If you're buying turn key properties out of state is fine and a property management company and a good handyman can resolve most issues you'll run into.

I use a separate email dedicated for mortgage business and a PO Box for all investment business mail that I check weekly.

These are professionals with additional training and a stricter code of ethics.

You certainly wouldn’t just give them back $1,000, much less $1,000 and a tax bill.