It was usually for a month or so and if they had funds, I let them in.

The guests have a credit card on file and your policy should allow you to charge for damages or excessive cleaning.

Both homes are now rented on two-year leases at $2,175/month.

By the time I reach 20% equity (likely 3+ years away), my monthly mortgage payment will come down when I refinance, but $600 is a big hit to the numbers. 

The only exception I use is when the property is a high-end unit.Informative title makes your property look like a cheap business but it is still way better than common titles like cute, adorable, cozy.If you are charging over 1k per night, I think it is better to give more high-end title like Stay with 30,000 trees, tingle your inner artist with lake front retreatJust my opinion :)

I've been trying to have one tenant do the autopayment for 8 months now and it has only worked one time.

If I own a property with a 1k mortgage per month and it stays empty (or I'm trying to evict) for a couple of months then I'll be ok.

Every 12 months you should budget 1 month of vacancy to turn the unit.

Monthly Rent Roll is right at $11,000.00.

I always advise to run a business for 3-6 months without an entity to see if it something you are making money in and something you want to continue doing.Once you have 3-6 months of activity, you have more information to provide to an accountant regarding income so he can provide suggestions on entity type.Best of luck