Price is the only thing that matters in this arena, every property is appealing at the right price.

Would I have to still pay the high taxes until I get them appealed and reassessed?

Learn the landlording ropes inside your own space and then branch out.Either way, if we're talking about long-term appeal, Denver's got it and ain't going anywhere in my book.

The location was also a huge factor...if this property would have been in an urban setting it may not have been as appealing.

Makaha, as already mentioned, is as far away from Honolulu as one gets on Oahu and the rental market is not very strong out there due to poor city planning means few jobs for young professionals and the inadequate roadway limits its appeal to commuters who want to work in the rapidly expanding town/city of Kapolei. 

If you are going to do this and plan to sell "quickly" you must have much more appeal AND a better price point then the others.

In my experience the mother-in-law suites tend to not be as big of selling points or have as much appeal for renting while looking for a multifamily myself.

Utter newbie here - first post.We own a small, appealing SFH in a desirable area of SE Portland. 

It might make your offer seem less appealing in a competitive market, so keep in mind you may lose the property putting in unusual contingencies.  

As people get older, retiring from the north to warm place like Tampa is appealing.