While the borrowing costs are higher, I’m exploring strategies where the returns could offset this.

Keep in touch with your lending partners for each one so you can understand whether you need departure residence income to qualify for the next or not.Finally, if you're investing with a Significant other, I recommend considering a "leapfrog" strategy where you buy one, then your partner buys the next, and so on.  

I don't believe "waiting it out" is an effective strategy.

I realize I am not cut out for the entire REI process of consistently finding multiple properties for particular exit strategies. 

@Dallas Smith To defer capital gains on your investment property, a 1031 exchange is an effective strategy, but the replacement property must be held for investment purposes for at least two years.

You can only sell it to landlords using the rent by room strategy.

I handle dispositions and tech; my business partner is more experienced with exit strategies and the finer points of investment.Hope this helps!

Solid strategy!

Most ideal would be seller financing, but open to creative strategies for a cash-flowing property. 

Anyone that is looking at your assets is always going to need to factor in property management, so you can show that as a real expense (and really make it as high or low as you want).I work in a vertically integrated real estate and development company, and I cannot imagine how things would run if we did not have an internal property management company that essentially works for the other companies but also stands on its own.