To make matters worse, I clocked an enormous profit the previous calendar year, so I owed a ton of taxes on money that I subsequently lost. 

We are there to make a profit  , plain and simple .   

Hi Alan,It's great that you're eager to learn about rentals and flips—both can be highly profitable if done right.

I wouldn't call that a true "DSCR Loan" - especially considering that a ground-up construction property won't have any cash flow so DSCR would be negative or 0 numerator if you'd try to calculate it ground up multifamily is not 0 cashflow there are hundreds of thousands of apartments built every year, leased up, and sold for a profit as well. we build not only at a discount for investors but 1% on infill lots I'd be really careful with all your absolutes. you can get land for 10k in columbus on lots you can build 2-4 units on in one of the cheapest construction markets in the country.

There are no economies of scale to build one property on one lot either so it ends up being more expensive for the builder which means they have to sell at a higher price in order to make their desired profit and if your market doesnt support this, then builder loses money.

Palo alto the 180 recently traded at 3.2 mil and the 350k one would be over 4 mil.. and would have cash flowed a ton :(  But you know I was at the time afraid of negative cash flow and I did make substantial profits on each that went into my business.. so not all bad.. 

Use your $40,000 to buy your way in, learn from some grey-haired guy or gal while on the job, and make a profit. 

In that case, it may be time to reap the profits from a rental property sale and invest elsewhere.

Many flippers try to buy in the fall and sell in the spring to boost their profits for this reason.

In August 2020, I took on what seemed like a great deal—a three-family property in Manchester. The seller was a terminally ill man who needed cash quickly to support his family before he passed. The lead came through ...