Consider the family who’ll eventually live there..maybe they’ll appreciate a second-floor deck accessible from a common hallway, where everyone can enjoy it, rather than limiting it to a single bedroom.

I know not typical on here to have such a little amount in loans but we enjoy great cash flow that we live on, have lots of flexibility in what we can do and have no concern about making payments if the economy were to take a dump.

I enjoy helping Bigger Pockets members and teahing all the loopholes I have found out over the last 18+ years!

This is my gamble.

I enjoy helping investors and other BP members avoid this very thing you just suffered. 

I enjoy finding creative ways to monetize normally overlooked spaces at my rental properties. 

However, though I don't know the actual numbers it seems like the home would offer so many more amenities I would enjoy as well.

These are very risk gambles that should only be attempted with money you don't really care about.  

At the end of the day, Panama City Beach and Destin offer more potential for consistent returns, fewer regulatory headaches, and the added perk of a beachside escape you can actually enjoy.

We are only very moderately leveraged, but I am in no rush to change that and rather use the cash flow to re-invest either into upgrades (we are doing a ton of driveways this year) or more RE.I don't think there is a right or wrong way, like you said there are many different ways, I just find myself adjusting every year a bit more in that direction. most condos historically are not great appreciation plays. its a place to live and enjoy.. unless said condo was bought in Miami in 2008 to 2010 :)No $#@% mate.And Chicago has been a disaster for many years now.I pinged Bri about it a while ago and she said "Good luck" hahaI guess it's more a trophy property than anything else during my "ego" pumping days.A bit older, balder and smarter nowadays I guess.Less is more mate lol