This is where I started making every land lording mistake mentioned in the first 100 podcasts on Bigger Pockets.

@Jonna Weber also hosts meetings every quarter with Bigger Pocketeers! 

Just from 10000 feet it looks like your gain will be just about what it was from the sale of the first property minus the $3K of loss your taking on this sale.The convention is that holding periods are tacked together when determining tax status. 

@Jose PenaWelcome to Bigger Pockets.

OR, do I do what makes me FEEL more comfortable because it’s familiar; and rent out my house, buy a bigger more expensive house that has potential to rent out a little casita that’s attached to the house for added income?

This is a big job - not necessarily a complicated job, but probably bigger of an undertaking than you think.You don't want to paint darker because darker paint will get hotter, and will then either warp the vinyl (which I've seen all over the place, especially in AL) or cause the paint to flake off - and that's where an inspector or an appraiser will get you. 

I'd be happy to answer any questions that you may have and go over various options that may work for you, but typically your investment is either going to be a loss (if you sell) or have a lower ROI than you initially planned as you will likely have invest another $30k to get it rent ready.There are some people pursuing legal recourse and @Aleks Gifford is a local person who is coordinating some of those efforts so  I would recommend reaching out to him.

@Gerald Savoy, welcome to Bigger Pockets and congratulations on your first post!

I would recommend 2x your current wage income in cash flow before retiring your wage job.I have a friend that has about 25 doors and was working a plan towards walking away and his company laid him off about 12 months early...he worked it out anyway, just less money saved, and now he continues to do new and bigger deals with partners.

I wanted to take this opportunity to introduce myself to the Bigger Pockets Community and to connect with fellow members.