On of the biggest scams/ money maker in the country , 

I think screening will be your best friend if you go this route to prevent the most headaches. 2) I'd say the biggest problem renting by room is potentially laws about unrelated persons living in same household.

Currently, funding seems to be our biggest hurdle in acquiring real estate. 

The biggest mistake is not truly understanding the exit strategy.

Some of these include:1) Your product/value proposition2) Marketing/Management/Customer Success3) Systems, Automations, Efficiency4) LocationTo me, #1 has the biggest weight on the success. 

Your clients will be coming to you for your expertise on what is likely their biggest asset and investment of their lives and keeping yourself up to date on the news and learning from others experiences is invaluable!

My biggest concern was that I have no bargaining power when its under contract on splitting repair expenses with the seller because I have to close on it.

It's my understanding that if there's a "partial exclusion", I'd use a Form 8949 with Code H...And if it's "fully excluded" and there's no 1099-S issued (which I indeed received no 1099-S), then I'd simply not mention it at all.But my biggest question is....

Your biggest problem is the same one all of us have down there right now - too much supply, too little demand.

This is one of the biggest mistakes I observe.While terms are important, take the time to get to know what each banker has to offer, their capacity and how they can help you grow.