Just like cross training for sports, I believe Real estate investing requires more than just real estate knowledge.

Win win.After all, "If you want to go quickly go alone, if you want to go far, go together" - African Proverb Love the "literally" comment :)This is definitely a team sport.

My PM company rep does a great job with tour operators, youth sports leagues coming for competitions and markets aggressively to keep their units full.

Ours were plausible triplexes BUT there was a bit of a gamble involved.

Very few have been operated as a business...most are, at best, a hobby, where the Owner enjoys doing handyman work (often of dubious quality), at worst, an absolute "investment" Gamble, with no regard for tenants, laws, or much of anything but spending the absolute minimum while collecting the most money possible until their "cash cow" implodes.

It also seems like a huge gamble to operate if I don't know quite for sure the variables involved to make a place have 33% occupancy rate on the year vs 75% occupancy rate on the year.

Stocks is gambling. 

If you wing it you will fail.According to (my) data with my selected assumptions, up to $5K spend on mailers is a gamble.

Most investors buy to make money, it seems you want to buy for the sake of doing a deal.perhaps you just want the appreciation and you'll pay the bills with your career income, just know that's gambling and we are in an appreciation slump for potentially a few years.

I'm not saying that you should pursue something as a speculative gamble, but simply evaluate a realistic perspective of where the market is headed.