I was able to get the HOA to approve the addition of another small dock right behind my house with a 23 x 8 foot slip 2 years ago.

Assuming you don’t meet the 500 hour test, you will likely need to document the time of others spent working on your property.In addition, you need to have guests at your property as well.Until you are 100% sure you can utilize the short term rental loophole, I’d wait to do the cost segregation study.

In addition to medical professionals, we also have college/grad students.

In addition to the Chula Vista bay front redevelopment, South Bay also has the Brown Field expansion.  

Actually more becuase now you are self-employed and have all of those pesky overhead costs. 

Know the strategy that you will employ and the numbers it takes to make a worthwhile return.  

Sometimes large employers will rent furnished apartments for their employees coming to town on a regular basis.Also, if you believe strongly in the appreciation of the house, how bad would the negative cash flow be if you did long term rental? 

I've heard of folks using the equity in their rental properties to purchase additional properties and I'm trying to learn if this would make sense for me.

In addition, you can listen to the Straight Up Chicago Investor for great local knowledge and contacts. 

Additionally I spent $35,000 on property taxes, $17,000 on insurance, $35,000 maintenance and repairs.