The issue with purchasing the property and then transferring the property into an LLC are the added transactional costs.

I always hired contractors, and did material runs for them several times a week after work and cleaned up jobs on the weekend, which was also time I spent at the properties, discovering issues, thinking about the rehabs and what needed to be done next.

Yeah..ok...And all teachers should have kids first...All doctors should have lots of medical issues before they can practice....All dentists should have lot of dental issues before they can practice...Every waiter should owner a restaurant before they can wait tables....Every car salesman should have bought multiple new cars before selling any....I get your point..... it would be great if every realtor had to have real life home ownership under their belt, so they have that BTDT experience..... but not gonna happen

Are there any issues with this strategy? 

We  manage inventory , are hospitable and curious with your guests , manage any maintenance issues and prep rooms for the next guests while  insure you obtain or maintain a Superhost status  -- I think that is very a fair tradeoff , If you listing cant afford that 15-18% than maybe that property is not pulling the numbers it ought to be. 

There are facebook groups where other Ownwerrez users help each other with issues. 

The issue now is that I'm not sure if I bid on a second mortgage or if there are multiple mortgages on the property.

I urge you to champion legislation that addresses these critical issues.

You focus on one relatively minor issue while missing the bigger picture.You have two properties, not one, for tax purposes.

Once recorded, the owner/seller of the property will not be able to close on the property without addressing this issue, thereby blocking them from cutting you out and selling to another party.Other than that, keep in mind it is VERY difficult to win in court for specific performance to force the seller to sell.Good luck, and keep moving forward!