If you have a building background, I would work with an architect and build some unique places that are stick built to hold the equity value better.

The pictures, while not great, are also not the problem.Across the country, it is hard to rent a place over the holidays.  

Just know you could end up chasing place to place which may work for you.

One has no mortgage, their other has a HELOC for around $20k remaining and is coming to its 10year term that was established before placing with LLC.My predicament is how/best way to pull equity out of either property for a down payment for the 3 family that is valued around $450k.

I'm not saying it's impossible, but it will be challenging.The toughest thing, by far, is placing tenants from afar.

These are not long-term rental properties, and our guests are traveling to the desert for vacation, not because they need a place to live for two nights on a weekend. 

North side Chicago I have never even had to give a tenant a late fee and none of the tenants I have placed for clients have ever given them issues either, properly picked people pay like clockwork on autopay.

Data suggests that both of these places have been on a decline for years.

This is a great place to learn and to connect with people so take advantage of all the great resources.

I would echo this, it is a great REIA and the best place to find local, like-minded individuals and resources.