@Sean Goodson the VA loan is incredible, but there are stipulations for when you can or cannot use it.

In my position I don't want to enter a property that doesn't cashflow in hopes that the market stays hot here....there is too much flux in the world for that imho...but cashflow alone is only part of the equation.Ultimately, this question was asked because I was using the calculators for the first time and doing my best to learn and expand my knowledge...and I wanted a little clarity around what I saw that didn't pass the sniff test.

Investing now Pros: 1) Immediate Cash Flow, meaning more money in your pocket. 2) Probably less initial investment capital needed than say 2 to 3 years from now.  3) Probably better interest rates, something to talk to your financial broker. 4) Probably hot market now for buyers, something to talk to your RE broker for specific states/areas, better chances to find a deal now with all this craziness today, 5) More appreciation on the long run due to typical inflation, 5) You gain more experience and able to jump quickly to the next deal or investment. 

Purchase price: $280,000 Cash invested: $8,500 Sale price: $340,000 4 bed 2 bath 1900sqft, hot tub, was going to be a buy and hold shifted to a fix and flip 1.5 years in.

Purchase price: $280,000 Cash invested: $8,500 Sale price: $340,000 4 bed 2 bath 1900sqft, hot tub, was going to be a buy and hold shifted to a fix and flip 1.5 years in.

I'm in a Hot Market with high prices where Cash Flowing properties are rare (Montreal, Canada)Would you be willing to take a deal with negative cash flow for the first 5 years (2-5K $ per year) if it offers:Appreciation potentialEquity accumulation ( Around 250K over 5 year)And tax benefits + deduction (Around 60K / year between operating expenses, loan interest and depreciation) ? 

You can't win every deal, especially when you know you paid too much in a hot market.

Those buildings tend to be very trendy, too - the new / hot buildings from 10 years ago are now dated and not getting top of the market rents or sale prices.

It's been incredibly weird to get this much money with strings attached,  only to have the lender go ¯\_(ツ)_/¯ when you try and get more clarity on the strings. 

Hot water must be functional.Pools must be functional and clear.Many of the above requirements are loosely enforced by conventional appraisers.