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?

The best banks that I have found based on your main concerns are smaller, regional, community sized banks.

I also look at it from the perspective of I now have extra cashflow to remove dangerous trees or do preventative maintenance to systems that have higher likely hood of causing damage.For the management I self manage for now so that fee just goes to me.

Unit 3 - mid-term rental (this would be best for the most private unit as most mid-term renters are more concerned with privacy and creature comforts than amenities)4.

The problem (as you have cited) is trying to understand what you need (you don't know what you don't know), where to get it, qualifying its source(s), and the validity and usefulness of all that.Pardon me if I've gone into this too much, but I meet many people with the same concerns that you are voicing and this is offered, as much as possible in direct response to your post.Please feel free to contact me if you have any comments or questions. 

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

Then tell us the nature of your remaining questions and concerns as to each remaining aspect, so people can have intelligent, focused, SHORT, conversations with you on each issue you present. 

It could certainly be a concern - but depends on a lot of factors - are you looking multi or SFR? 

It’s the most dangerous thing we do everyday, we carry liability insurance through our personal auto policy.

It would certainly help to dispel all of the very real concerns we all have right now and potentially ease some minds for both current and future.