While your renters pay down your mortgage you can take advance of tax benefits, appreciation and cash on cash returns.. building your net-worth.

Do you have any experience \ success in making an offer on multiple properties in order to gain higher discounts?

There are many reasons to manage your own rental properties, but being able to fill vacancies when and how I choose is definitely one of the greatest benefits to me.

Here are some additional benefits it has over SD IRA:Great tax-shelter: contribution limits nearly 10 times higher than an IRA (up to $60K/yr)Exempt from UBIT on leveraged real estateGreater protection from creditors Ability to invest tax-free using Roth (post-tax) component Lower cost since there are no custodian, asset-based or transaction feesand more!!

When you have a clear definition of the tenant base, you gain clarity on which strategies to pursue and can provide a better product to the market, which tends to improve one's odds of success. 

Does it make sense to hold the condo and rent it for a period of time to capture any tax benefits?

In that situation, you will have to weigh out the benefits of having that cash available to you versus changing the terms ( potentially higher rates/higher payments ) on one or all of those properties.

I need to analyze my financial situation to see when is better to pay capital gain taxes on our rental property we are selling- this year or next. 

Also try to aim for a duplex to enjoy the benefits of househacking. 

I have properties with tenants in place so rent roll and P&L is obvious but what else will help benefit me the most?