Our 3-season property (mud season is slow) has us at 107 nights this year.  

The way I see it, I have the following choices:Option 1 - Get a Wyoming LLC for anonymity, which holds the LLC the owns my rentalOption 2 - Get an LLC in my home state that owns the LLC in whatever state I buy a rental inOption 3 - Get an LLC only in the state that I buy a rentalOption 4 - Don't get any LLCs because I don't have enough property to need it and get an umbrella policyI am officially stuck in the mud trying to figure this out.

You bring the deal, the partner brings the money, and you split the returns.That said, either your friend is being really generous or there might be something wrong or undesirable about these properties.

Skim coat the walls with drywall mud to get it smooth or smoother. 

Ditto with the time and cost (possible evictions) of getting rid of undesirable tenants, not to mention the risk of additional unforeseen damages when unhappy tenants have to move out.Mom and pop owners are notorious for not counting expenses, not the least of which is their own labor and management.

Today, The city offers a range of attractions, from our world-famous baseball team, the Toledo Mud Hens, the Minor League hockey team favorites The Walleye, and the Toledo Zoo, to increasing world class Toledo Museum of Art, and a vibrant art culture.

I hope this is clear than mud, those are the issues I see to the situation.

The main floor offers hardwood floors, mud room, laundry room, kitchen with stainless steel appliances, living room, fireplace, powder room and plenty of natural light.

I have a budget of 300k sale price, and would prefer to avoid really bad areas that attract undesireable tenants.

All they do is drag my feet through the mud.