I'm considering self-management and I'm in the process of setting up systems for it.

At the same time, by the time the market increases in price I will be paying 1K per month towards the mortgage to cover what the rent wont cover, so its 12K per year of loss (if I get a good tenants and nothing breaks), then who knows even if the market does go up...

@Jonathan PantagesContact your local self-storage facility, and see what it costs to rent a unit to store the tenant's items.

I have some cash coming my way soon and trying to determine if I should use some of the cash to recast some of my mortgages to increase cash flow or not.  

This increases the property's value and can allow you to charge higher rent, improving your cash flow and the property's appraisal value for refinancing.Rent: Lease out the newly acquired and rehabbed properties, preferably to reliable tenants similar to the family you currently have in your townhouse.

Most visitors and lurkers are new to real estate, that means they don't have the experience and confidence you and I have.

I've self-managed mine remotely (4 hours away) for almost a year and a friend is asking that I manage his house located about an hour north of mine. 

I am looking to increase my cash flow to support my family and wanted to learn more about real estate investing.

It just increases your exposure.Not sure how you do NOT have an insurance policy and still have a mortgage...We've got plenty of threads, pretty much daily, about the LLC question...  

It is about an hour from us and we currently self manage (16) units.