Your responses make it clear you are indeed working hard at this! Keep up the effort.
TL; DR - not sure I have all the answers, can only share my thoughts. Doing so for questions raised, all of which are very good questions:
Your first-draft plans all add risk into a risky situation. It seems you are hoping to get a higher return but engaging in wishful thinking. You will likely end up with more problems, not more income.
I sympathize that his skills are manual, and landlording includes some manual fix-it labor. But the other aspects make it too risky.
Can you please clarify on the risk? Are you thinking we are looking at bad properties, or that there is too much ambiguity on his benefits? Something else?
Something else:
1. Belief on my part that real estate is more of a business than a passive investment, coupled with the perception that the team of you and dad is not yet knowledgeable enough to make success likely.
2. Since I feel that real estate is a business, and you say he will not be able to sustain much work, I assume that over the long term you and he would add relatively little value. Or more accurately, there's a risk that you wouldn't.
3. Costs. From what I can tell (longtime landlord, just one property; medium amount of reading) costs over time are often higher than inexperienced landlords estimate.
4. The effect of leverage. It magnifies the good and the bad. If you borrow to buy a profitable property, and do so at a cost that is less than the property earns (your cost of funds is less than the capitalization rate), leverage raises your profit. But if your cap rate turns out to be less than your borrowing cost, leverage magnifies your losses relative to other investments at that cap rate.
In other words, I'm worried you guys will try your best but lose money.
I took care of my dad in his older years. It took a lot of time and involved numerous twists and turns. One of them was an owned property that he didn't live in any more. We ended up with no rent and three years of expenses followed by selling at a loss. I'm glad my own property has been profitable, but his wasn't. Financially it was a time suck and a money sink.
Before you do any plan, please consult a very skilled expert (attorney?) who truly knows the details of how all of your father's benefits can be disqualified. That is the part you have to get right. Then choose the path that involves the least number of screwup options.
Any advice on finding a good lawyer for this? I just replied in another post, I have tried this in the past. Finding a competent lawyer seems really hard here. Locally they don't seem to exist, and internet ones don't seem to have enough local knowledge. I'll happily pay the lawyer fees to get the information locked down, I just haven't been able to find one to pay that actually knows the answers.
That's a problem. I grew up in a town near big rural areas, so I sympathize.
Still, are his benefits federal? If so, wouldn't that mean an expert anywhere in the country could explain the rules?
If so, it seems like the internet must lead to someone competent. When I researched issues related to my dad, usually the internet had multiple sources.
I'd start like you did - search for something like "can i work and still collect ssdi"
I got:
https://www.google.com/search?q=can+i+work+and+still+collect+ssdi&rlz=1C5CHFA_enUS692US692&oq=can+i+work+and+still+collect+ssdi&aqs=chrome..69i57j0l5.14145j0j7&sourceid=chrome&ie=UTF-8Several sites explaining the basics look like they give overview.
Then I'd search, perhaps using LinkedIn if I didn't like Google's results, for lawyers or consultants using various search terms from the discussions. Figure out who has real experience with this work. Maybe look for "reviews" of these people. Maybe contact multiple ones - five, ten, twenty. Seems like expertise to back up the general websites should be findable for major federal programs.
If you just sold the house and he got a $400 check per month (withdrawal from the resulting investments that you set up for him), you might not feel he's out of poverty. But how would he feel? Would he be glad to get the check?
He has told me he basically needs another 1k/mo to feel comfortable, assuming he keeps all his benefits. I currently give him 800-1000/mo to keep him living.
If you then knew he is allowed to earn up to $1170 in handyman income, how would he feel about that?
It's not sustainable long term. He already has major health problems. I figure he could push for another couple years and get settled on things, but he does also need a retirement strategy. I agree that the handyman income could help him survive on his own for another few years, but it doesn't get him ahead, in which case he is back in a huge problem with no changes in a few years.
Ok, clear and understandable target. So the $400-500 from selling the house and investing the proceeds in financial investments would cover part, but you and he would still want him to have another $600/mo or so.
If you don't have a better option, "he earns about $600 while he can" would then limit your contribution lower amounts and fewer years. You'd still face the pride issue, but only farther down the road. As my dad got weaker, he became more accepting of help, but you could have a different experience.
I wish I had a better suggestion, other than set up the $400-plus-handyman thing and urge him to save during months where he earns more than $600. Still, my personal opinion is that "huge problem" and "my son loves me and helps me out with $500/mo now that I can't work any more, while I get $800 in benefits and $400 from investments" are two different things.
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I very much respect your consideration for Dad's feelings. You obviously love him, and his situation sounds like his desires are greater than his resources. You will decide in the end what you can contribute and how. You'll find out from experience what works and what doesn't. We can only guess what will work, what the pitfalls are. You're the one who will really do it, so in the end, do what you think is right. In any event, your dad is lucky to have you. Best wishes in this.
Fwiw, my experience of aging parents is that everyone suffers from aging in ways they don't like. It varies from case to case what the specific suffering is, but some of the suffering is inevitable. I took solace eventually in distinguishing between inevitable pain versus avoidable pain. Some of your dad's pain is unavoidable, so - yes feel empathy, but don't try to fix the unfixable if it puts the avoidable pain at risk.
I guess I really saying that I suspect the landlord route is adding avoidable pain, risking loss of the investment. But possibly you will pull it off and be glad that you ignored my guess. Best wishes either way.