I read the post knowing it would likely remind me about all the times I read the handwriting on the wall and decided it was a message for someone else.

I hope you find a good place to land. I know it has been a while for you but you are still motivated and focused on the right outcomes. You will find a niche, maybe not the one you expected but you will drop into a groove and realize that things are looking up for you and your Mom.

I understand the whole home ownership angle where you could liquidate an asset but would have to absorb a loss in the process since the place needs some work and you can't afford to do it yet. Hang on to the houses, all of them. They can be your landing zone or safe spot.

We have a home that we have leased out for around 30 years. It has always been the best in the neighborhood because I did the work of maintaining and upgrading it myself, along with my wife and part of my family. I would sell it now but it needs siding and the bids for that are way out of my price range so that is one of the next DIY projects for me. I just need to get a tenant into it ASAP and that will allow me to make it happen. The materials to do it cost under $10k but like your property, we have had years where we made money on the house and years where we barely covered or lost money due to maintenance items or other ownership costs.

Leverage any opportunity to work with local contractors swinging a hammer bending nails or using a saw to shorten boards. That can be a path to obtaining scrap materials or unusable items that would go to a dumpster. Contractors have to pay disposal fees so anything that allows them to reduce the size of the load saves them money when the job is done. Warped or curled dimensional lumber can be straightened at home. Half sheets of plywood or siding nail up as tightly as full sheets. There is a place for all that if you examine your needs and keep an eye out for things that can be made to work.

My grandfather built a business as a home-builder by first building a home for himself and my grandmother to move into as soon as they married. He got the materials by asking around with locals who were working on their own places and inquiring about whether he could have the scraps and cutoffs. He ended up needing to buy nails and a few other small items but he built a house with materials that cost him the labor to clean up building sites. Once he finished the house a local man who had been watching the process offered to buy it from him. He sold that house and took the money and built a new house with new materials and moved in with my grandmother to a much larger, much nicer place than they would've had. Others who knew him and watched the process approached him about building things for them and in no time he was building houses, church buildings, sheds, etc all over the region. He built custom homes until he passed away about 60-65 years later.

Since it appears you may be up around Syracuse, Ft. Drum is right down the road. One of my brothers got the money to start his own business by driving for Pizza Hut. If you can get established as the pizza guy on a base like that you're on your way up. Soldiers tip well. Pizza is a huge seller. You do need a base pass but I think the pizza outfit sets you up. He would always bake the order and then bake several extra pizzas and carry it all onto base. By the time he had dropped off the pizza that had actually been ordered he had a line of soldiers hoping to get one of the extras. Pizza is great food option. Many of those guys became regular customers. He made great tips and sold lots of pizzas that otherwise wouldn't have been ordered. After a couple years of pie-hawking during which he was also mowing yards and trimming trees with a friend who had a local tree service, he took money he had earned and bought himself a new mower and chainsaw. That was 10 years ago now and he grossed $300k last year with one employee doing nothing but tree service. He has a bro-dozer truck with large dump trailer to handle the wood and debris and he rents other equipment as he needs it.

Pressure washing can be a real winner too. That's one thing my brother has mentioned branching into. Staining fences and decks. Cleaning gutters. Washing windows. Caulking siding and painting.

There are lots of services that people need that don't take much investment. Door hang flyers with contact info and let people know you are available. Visit a t-shirt printer or embroidery place and have them make a few shirts with a reasonably memorable logo or slogan and your name and contact info. Wear them to the grocery store and home improvement store and let people call you.

I have several gardens I built to help manage food costs. It is unbelievably easy and satisfying to be able to open my door and select a few herbs from my pizza garden while my pizza stone warms up. We have a wide selection of all the things we enjoy eating and some we want to try. Fruits, nuts, vegetables, herbs, berries. So many things are easy to grow. That can help you manage your food costs and improve the quality of your food at the same time.

Good luck to you. I don't think you need it though. Your heart is in the right place. All the other things will fall in line behind it.