I just completed a small subdivision myself - just a word of advice that if you do sell any of these you'll need a release of mortgage from your current lender to do so.

(Unlike mortgages.)

For the $525K property, with the low mortgage rate(you will probably never get a such low rate), it might make sense to hold onto it for now, especially if you can still sell it as a primary residence within the next three years and avoid capital gains taxes.

The Numbers:Cash Flow Analysis: Investors typically look for properties that will generate positive cash flow—meaning the income from rent covers the property’s expenses (mortgage, taxes, maintenance, etc.) and then some.

My unit cost 3k/month to rent but you can get cheaper units for much less.

 @Jessica Frisk I would not be keen on the 15-yr fixed rate mortgage if that makes you cash flow negative.

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

Credit score shouldn't be the primary driver of tenant approval, because if they could qualify for a mortgage they probably wouldn't be renters.

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They also could have a mortgage that could not be satisfied by the price and in that instance, again the bank would not release it - so again stuck.