I personally self-manage, but @Mark Byers a rock star when it comes to managing properties and understands Section 8, so you can benefit from Government paid rent - which I highly recommend. 

Like you said though... it's a bit of a trek to the beach.We fell in love with Jupiter in a matter of hours.

I dont have any particular advice other than an antidotal story.I saw and add in a mag in 2000 for ski in ski out condos at silver star ( merrit )  for 49k CDN which at the time was US 35k. so i got to check them out. fall in love with the oakanogan valley and bought instead a home at the oakanogan golf clubbrand new 210k CND  which at the time was just over 165k US.. 2 story walk out 2400 sq feet.. etc.. so spent a year there and got a season pass to big white.. that area rocks.. good luck with it..

Zillow is definitely hit or miss in Houston they rate themselves a 1 star for the Houston market:http://www.zillow.com/zestimate/If you feel like you aren't getting great property management service I suggest you change property managers.

So if you dont have any personal income you will need the rent to price ratios to work out so that this formula will qualify the entire mortgage/tax/ins of the property you're looking to buy.Example above for orange county will not work, but for midwest might due simply to higher rent to price ratios of mid west versus subpar RV ratios in OC, california.In CA gross rents are .3 to .5% RV ratios while in the mid west you can get 1.5-3.0% RV ratios a star difference.

I know the basics about saving but what can I do now to get a jump star?

I think its important that those of use that are enjoying smooth sailing speak up as well, otherwise all we'll hear about are the horror stories - much like how all yelp reviews are either 5 or 1 star.

I then spent 10 years working as a comic book writer and letterer while raising my children and moving from 5-star resort to 5-star resort where my wife opened and developed spas.

Hello BP superstars (and rising stars)! 

Once I received my first few 5 star reviews and I gained some confidence that my listing was not only desirable but sufficient and enjoyable during the stay I moved away from smart pricing and have almost doubled the nightly rate with no hiccups.