If you're up for some delayed gratification and tax free cash, I think it's a fantastic idea.I would recommend starting with a paint, flooring, kitchen, and bath renovation - more of a cosmetic fixer that can still qualify for conventional financing.

It's a learning curve, but I think it's going to be the best solution. 

(b) Is it okay to talk to multiple realtors at the same time (I'm thinking it would be better to have a separate realtor with lots of market knowledge and experience in each of the mentioned locations) or should I only plan to use one?

What do you think your home would rent for?

In your opinion what do you think is the best property to start with?

No, he's not an architect, he drew all designs, floor plan, site plan, etc, and we had a structural engineer design his part, and paid an architect to sign off on them.  

Quote from @Trent Reeve: i would think they would have more amenities than a non-condo.I think the reference was how do you stand out from one condo to another when they are all identical, vs how do you compete with single family homes.

I think Rooms to go would be a good option to get you started given your distance.

I think it’s crazy that they travel so far, nice but great. 

They list properties on their own site, plus Airbnb, VRBO, Booking.com.