You just have to get in the game, learn, and adapt as you go. 

As for property management software, options like Hostaway or Lodgify can streamline bookings and communication.

Although I probably get killed on transaction fees which is part of why I am not pulling the trigger (along with lack of time to execute well).There are games you can play for increasing your returns in the stock market (sector rotations, rebalancing, being a good company picker) but you lack operational control. 

So you will need to have skin in the game.

That way you’ve got some skin in the game, and the tenants will be less likely to protest that the other tenants are using more electricity or gas.

I would guess that you have little or no experience running any kind of STR, and now want to get that experience on the back of someone else's investment, with little or no personal skin in the game, and that's not a good way to build an investment portfolio.

Use next 4-6 months to learn by listening, reading and watching how the real estate investment game works.

For me, I’ve been testing a few different methods recently, but I’m always looking for new ideas to take my wholesaling game to the next level. 

Unfortunately, we picked a bad time, because a game just finished, and people were streaming out of Wrigley Field.

My dad and I (both with access to VA loans) are about to get into the multifam game and how we proceed is really going to depend on the true occupancy rules for the VA and our lender.