Thanks for the comments all, I appreciate them, both positive and negative ;)
A few things:
1) Disability - This is only applicable in that I can't 'work', and that I have to consider how I 'earn' money. Anything I have coming in must be considered 'unearned' or 'passive' income.
2) Age - My age is primarily a factor inasmuch as the time it will take to achieve my goals. I am not looking to get rich quick or anything, and my goals are quite modest. I am mainly curious about the practicality of putting in the next 12-13 years to achieve some measure of reliable income.
3) Madness - I am honestly not sure why you think investing in real estate for me is madness. I am sure that a fair bit of skepticism is warranted, but 'utterly catastrophic' seems a bit hyperbolic.
You indicated that my financial situation was 'precarious'. I disagree. I accept that it isn't optimal, but then again, if it were, I wouldn't have even considered investing in the first place. That is, after all, why I am where I am currently.
Either way, let me describe my financial situation and my plans and see if you still think I am mad.
I currently receive $1650 a month in disability. My wife and I live frugally but comfortably on that amount. My house is paid for, my other house has a mortgage but that is also paid by my mother. If she were to die, I would sell that house immediately. I have 2 cars that are paid for, and no debt at all, except for the house I rent to my mom.
My assets include $58k equity for the house my mom rents, $70k for the house I live in. $58.5k in my 401k (Because I am disabled and no longer working, I am not able to deposit any money in this 401k. I can either let it sit and pay fees or convert it to an IRA or cash it out (again , no penalty because I am disabled). My wife has 10k in her 401k. I also have a Credit Card with a $10k limit with an interest rate of 6.25% There is no balance on this card. I also have 15k in savings, but this is our emergency buffer and I won't be investing that.
Potential assets include 2 worker's comp settlements that we estimate should total $40k-$45k. Additionally, when my wife is approved for SSDI, she will receive around $1200 a month in disability.
In terms of disability income, I will ensure that whatever I do will NOT affect this income. This income will not be put 'at risk'. By this I mean that any debts, loans, mortgages, repairs, etc., will not have to be paid for out of our disability income. I will ensure that I have a cash reserve that will cover any reasonable expenses.
For example, if I cash out 45k from my 401k, I would reserve 5k to cover expenses that are not covered by rental income. If I get a mortgage and for some reasons the house was vacant for some months, this would be paid for by the cash reserve.
As long as I plan effectively so that our current income is not at risk, my only risk would be what I choose to invest from our assets. If my investments failed so spectacularly that I lost all everything I invested, our lives would remain unchanged, except that we no longer have a 401k asset. Frankly, this asset is small enough that the benefit of not putting it at risk is fairly small. 60k isn't going to make much of a difference in the grand scheme of things. It mainly means we may not take as many vacations.
This leaves me wondering...
What exactly is it about my situation that you deem it so perilous for me to invest?