As you can see, the tenant must pay a portion of the rent and they are often late.

Zillow suggests that I spend $29.99 for a premium listing, promising that renters will see the listing more often because it appears higher in search results.

I could give you a pretty solid estimate if I could see things better on the items you listed. 

I don't see the value that a wholesaler could bring to the equation in an apartment sale.

After they see the full benefits (decreased living expenses, appreciation, debt pay down from your tenants, depreciation), then their mind will change :)What is the business plan transitioning from HH#1 to HH#2?

@Andrew Syrios Tulum  ruins of course and if you can make it Akumal to see the giant turtles eat under the sea!!

I see the hassle of transferring a property you buy into your name to an LLC because I would like mitigate the possible legal risk of some issues that could occur if something happens with a tenant on one of my properties and take advantage of any tax laws with a property inside of an LLC. 

I bought sight unseen out of state (Indianapolis) - I don't recommend this but I do know experienced investors who buy OOS and never see the property in person but they have a  higher risk tolerance than me. 

It might be worthwhile to focus on neighborhoods that are on the cusp of development or have strong local amenities, as those often see the most appreciation over time.

It's a slow process, but very worth it once you start to see the results