Some quotes stood out to me
> ...in fact I own three houses
> ...I left behind everything and everyone i know and love on the west coast to come to New York specifically for this opportunity of helping care for my family and growing long term equity with real estate
> With my full time engineering job bringing in around $150k, a salary that I clawed my way slowly and steadily for 20 years, I could just about manage covering all the expenses, maintenance, and planned improvements for the long-term vision of the properties, maintain my 16-year-old daily driver car, and maybe even have four or five thousand dollars left over each year to take one little camping trip and make a couple stock and crypto investments.
Rather than building a career as a software engineer, he spent most of his time as a small-time real estate and crypto(!) investor subsidized by his software engineering side hustle.
lumping in a camping trip with investments is odd. A camping trip might cost very nearly zero dollars, depending on distance and what I have available. We'll be generous here and assume $100 was spent for some reason. That $100 is expended, you don't get it back.
A stock investment might "cost" $4000, but I would hope to have nearly $4000 in some asset. My absolute worst investments, I typically still exited them with 40% of my initial capital.
i was just describing the all around comfort level of my lifestyle. if you drive a couple states away for a camping trip for a week, get a couple motels maybe, eat out, etc, it can be 2k$ pretty easily
I think it's clear he considers the real estate to be actual investments, but the camping trips and crypto/stock to be "play money". Perhaps not a bad strategy.
As much as I have sympathy for dealing with an aging family and being a caretaker, it's these three quotes that essentially threw me away. I'm in a similar position and will never be able to afford property or a home, let alone three houses and the ability to throw a bunch of money at crypto despite having a salary at a similar level.
It sounds like there were poor investments made in owning a bunch of property and now that issue is coming to roost.
And somehow thinks upstate NY is a better real estate investment market than California.
I was just trying to become a homeowner. my first house in new york was about 1/4th to 1/5th the cost of a "starter home" anywhere in california. I was never going to be able to afford that
I don't want to sound like I'm victim-blaming here, but the reality is there's no free lunch. Investments are not risk-free, and, as you've discovered, there's a reason you got these properties at such a low cost. It seems like your real estate situation can't go on like this forever, right?
> selling my properties would be a ruinous move letting go of my most valuable assets that are the only toe hold I have in this economy, and may threaten my ability to become a homeowner potentially ever again, depending on how this economic future plays out.
Despite these negatives, it's possible that selling is the financially-smart thing to do. Keeping your properties may also be a ruinous move that could cost your ability to become a homeowner ever again. It's unfortunate, but it sounds like you need to choose whichever is the lesser of two evils and stick with it.
> If i was bestowed some gift of capital, I could complete the renovations and make the house income-producing.
As an alternative, if this is actually true, then you'd be the perfect candidate for a loan against your house. People commonly get emotional around housing and debt, but there's no room for that when you're struggling to survive.