Learn to outperform the market by looking at property entry values and resale values based on improvement.

If I am selling a car and just put it in my yard with a sign, it might sell.I will have a much better chance if I also advertise it on FB marketplace AND Craigslist in addition to putting it my yard.

Something happens in there job, your head could be the price of there career improvement. 

As I addressed in another discussion, most money in real estate is made by long term appreciation and by improving, repositioning, and stabilizing the property, NOT thru purchasing at a discounted price.  

This could improve your margins.Occupancy Rate: A 60% occupancy rate seems low for Jax Beach, but that is a reasonable conservative baseline. 

Over the past 6 months I have been really researching and devoting myself to self improvement and learning.

And keep in mind that the rate on the 2nd lien will likely be 10-12% so depending on the cash flow it might not actually yield that much cash to you at closingMore importantly, it's just more debt so ultimately it sounds like you need an income-producing event to actually improve your situation and avoid some of the consequences that you mentioned

So much so that when we do come across that all-to-rare exception of a person who's grinding at improving there life, to elevate, it's notice, it's a shocker, and we go the extra mile to really help them if and where we can. 

There’s also a small chance this means “not done/not attempted”. 

As to the buddy I mentioned in Washington state it was the same scenario; he converted tax-free up to their standard deduction but above that he kept within the lowest tax bracket and paid the smallest amount of tax possible.Thank you @Basit Siddiqi for calling me out on this and giving me a chance to address my mistake; it's important people have the correct information.