The best deal I ever made was through a friend of a friend of a friend I landed a slot on a boat and was able to work the 1980 and 81 king crab seasons in AK. It only consisted of a few weeks each year but paid amazingly well. Looking back historically it was what is now called the glory years of Alaskas king crab harvests.

After the 1980 season I was able to pay 40K cash for a sorta non-livable old house on 40 acres in the Flathead valley in MT. It was my castle, it had power, water and a wood stove but no septic but a fair outhouse. It needed work and so did I so we were a match, I'd been living in a slide-in pickup camper prior.

Due to a lot of deer meat and low overhead I made it til the 1981 crab season got under way were I managed to double the wages I'd made the prior crab season.
I returned to my humble MT abode and promptly spent all my earnings on a commercial property in the Flathead that provided a slight income but It needed lot's of work....and once again I was broke, I'd spent 80k cashing out the property. No real job, no credit to speak of equals no loans.

I had to sell the 20 acre parcel next to the one the house sat on to get by the next few years. Managed to get what I'd paid plus enough to pay for getting the remaining 20 acres surveyed and broken into 40, 1/2 acre lots but had to dump the other 20k into the commercial property in attempt to enhance it's monthly revenues.

Fast forward 15 years...A real estate boom had hit the Flathead Valley and I sold both of those properties.

The commercial property was then bringing in over 100k a year in rental income, It'd now paid for itself a few times over, it sold for 950k.

My beater old house was still the same, no septic but an upgraded outhouse and a better wood stove, those 40 half acre lots were then worth about 35K each.
I sold to a developer for 800k.

Everything hinged on those few short weeks on a boat in Alaska some 17 years prior and having the balls to go for broke or bust. So, that was the best deal of my life.

I had to reinvest the bulk of the monies to avoid getting hit hard on taxes, 1.5M went back into Flathead Valley properties which since have more than doubled in value and are now self supporting tax and insurance wise with a little monthly residual.