What To Do With Homes Not Purchased As Investments?

[Account Closed]

I own a condo I purchased as my first home in 2008 and a single family home I purchased to move into in 2013.  Neither were purchased as investment properties.  I moved out of the second property in 2017 and I have had good luck keeping the properties occupied using a local property management company.  The condo value was less than I purchased it for when I moved out which is why I kept it to rent out.  It was so easy to get tenants that I decided to do the same thing with my previous home.

I've started learning more about analyzing real estate deals and realized that while I'm paying down the loan on both properties and they are appreciating, I have negative cash flow on each.  I recently read the The Book On Rental Property Investing by Brandon Turner of Bigger Pockets and I know have a much better understanding of what these properties are actually costing me.  The cash flow on the condo is -$125 per month and it's -$110 on the other house.  This includes budgeting for vacancies, capital expenditures, repairs etc.

If you count mortgage paydown the condo increases my net worth $155 per month after negative cash flow and the house increases my net worth $230 per month after negative cash flow.

I would like to do more real estate investing and I can't decide if it makes sense to keep these properties or to sell them and start over.  I feel like it makes sense to keep them because I will lose so much to real estate commissions when I sell and closing costs when I buy a new property.  That being said, there's so much to consider I'm not sure where to start.

Please let me know what other information I can provide.  Thanks in advance for your help!