I.E. you know the area better than others.Is there a short-term rental market where you vacation at, where you went to college or where you grew up in?

Those in other markets will not be impressed. 

I read “if your parents can’t afford rent, you can claim fair market value rent and claim the amount they actually don’t pay as a gift from you to them.

Quote from @Melissa Stanley: A "cosigner" is someone that is financially responsible but not an actual occupant of the rental.

Do most sellers prefer shorter terms (5-10 years), or can you actually structure something close to a 30-year term like a traditional mortgage?

He actually has open maintenance tech positions on his job board, etc.  

Keeping in mind you're not making a decision for your forever home....Let me know if you need market specific insight. 

However, many states now require some version of a license to wholesale, so I'd identify a market first and then dig into their specific wholesaler requirements. 

Yes - and even when its out there its typically impossible to qualify (need high rate and high DSCR and typically would have to qualify as a LTR - so almost a unicorn or in a really bad market)

However, you can actually end up in a spot where you have no Federal Income Tax, but you still owe Self Employment Tax.