The last time this sold was actually 2002 for $149,000 below is a link to the county web site on it.https://beacon.schneidercorp.c...The property is not zoned as a rental and I would think can’t be due to the density of rentals in the area.Hope this helps.

There are web sites that compile basic data like that.

A handful allow a month or more...not day by day....some people say renting 30 days or more to one tenant can change the STR to someone with tenant rights, so some operators won't do that.I've also seen condo associations prohibit or restrict even LTR, so that does happen.You could be entirely right that state law supersedes HOA CCR and R&R, but is that a fight you want to fight and pay to fight and gamble on big lawyer fees?

It's all a gamble, barrier of entry aside. 

In Hawaii, you're mostly having to gamble on appreciation, which is just that -- A GAMBLE. 

I was searching some real estate analysis softwares and found there are couple of web based software  that also have database and comparable for all US properties.

I probably will try this service when I have new tenants.As for web hosting, there are free platforms such as AwardSpace that you can use if you know how to build a website.

No idea what my roi would be, it would be a complete gamble.

That would never happen for me, since other than gambling, I could never achieve it in a two year time frame. 

Does anyone have experience with the online tool called 401k optimizer.  I am trying to build diversification in my financial plan and want to keep my tax advantaged monies in the market as opposed to leveraging into ...