I HATE the idea of not being able to access anything that I need online.

@Leslie L Meneus, while the forums can be pretty good, in-person networking and sharing ideas is much more valuable.  

Any idea of lead times? 

Starting with local credit unions is a good idea.2 - I recommend starting your search with a Realtor who specializes in working with investors.

But given I've paid for snow removal like once ever, I don't know what I should offer someone who is not a "pro" and already has an idea of their rate. 

I love the idea and its really quite nice because the costs are minimal and upside is huge.

It’s a good idea to work with a qualified intermediary and a tax advisor to ensure everything is structured properly and you’re clear on any tax implications.

Would love to connect with local RE agents and have an idea of the market situation in SA.

Happy to connect and share ideas!

We like the short-term rental idea because we could stay at the property ourselves when we want - summer break, spring/winter breaks, etc.Our budget will be right around $1M or less ideally, and we would like a short distance to the ocean.How likely is it that we could find a property as described above and have it cover or come close to covering the mortgage?