I know in theory I should take the monthly savings and start applying it on a monthly basis to the home equity but the reality is I haven't been disciplined to date and don't necessarily see that happening in the future. 

That is why you really need to take an honest assessment of the reality on your property.  

Reality is far different than theory.Read "Long-Distance Real Estate Investing" by David Greene to learn how to analyze a market and build a team that can help you avoid these mistakes.

In reality appraisers are a lot like Agents.

My only issue here is that I have about 190k saved (mostly invested in the s&p 500). 52k of which is in retirement savings accounts and 13k of which is in an HSA, so in reality I really only have 125k to use as a down payment and closing costs, or 150k if I take out a loan against my 401k. 

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

The reality is that listing agents here have been burned by national lenders who don't understand the nuances of our condotels and oceanfront buildings and end up not being able to underwrite the deal. 

This surely is a big reality check!

In reality, you would start looking at least 4 months to go in your lease and then hopefully find something before the lease is up, saving you that 3 months of 6600.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!