You can sell with a monetized installment sale, which results in 30 year deferral of capital gains tax, and provides you with 93.5% of your net sales proceeds in cash.

The market sometimes (but not always) gives us gains, tenants and time result in paid down mortgages, which results in equity increases.  

When you later sell that property you will not get the full amount of gain tax free as with your other primary residence. 

And I'll turn that into 10-15% gains, or much more...

Reap the benefits of what you have gained so far, most likely almost tax free.

I like to know everything I need to know and gain tips and advise on how to find a starter homer hat meets most of my needs. 

This is commonly referred to as the BRRRR strategy.If you are looking to grow a portfolio to gain passive income to replace your current income this is a perfect strategy to use.  

I am not necessarily saying you have to use all of your gains from the primary residence for a new property. 

I will list the numbers:current rent $1950/month (going to $2000 in about 6 months at end of 2 yr lease)My expenses: annual taxes $7950 ($662/month)                        Heloc balance $170k interest currently 5%                        land lord policy $1150/ year                        Self managed                        Maintenance : has averaged $300-400 per year.Reasons I am considering sale :   1) property is currently worth about $270k (making me feel roi is low).                                                           2) property has a pool which is a liability that I'm not completely comfortable with.                                                           3) property has a heloc balance against it of about $170k that I technically cannot deduct the interest                                                                       because it wasn't used for the property or any other rental.                                                           4) Tax treatment: my understanding is if you sell it having lived in it 2 out of last 5 years the capital gains                                                                 would be exempt. 

So for the extra $20 a month I would have to invest into wifi extenders but end of the day I will be gaining..