You're going to have that challenge no matter when your contemplating a sale.So the key is something you hinted at in your op. 

The capitals gains hit would be around $38,000 but I feel like that is the smaller number compared to reinvesting now via 1031 and paying these super inflated prices only to be in the hole later.I am contemplating selling and holding for a few years or possibly using the sale to pay of my primary homes mortgage which would save me $135,000 in interest.

Originally I was looking to purchase a SFR that I could put some sweat equity into and rent out at some future point but lately have been contemplating a duplex in order to house hack.I have been combing through the forums and information on BP but would love any advice or suggestions for additional research I should perform. 

As I explore my core 4 and look into different markets I am contemplating on a couple different places where the entry level is more do able to compound a strategy, and implement the notorious BRRR.

If you're not contemplating rehab or are already in leasable condition, you'll be able to get a 30 yr fixed against the property on a DSCR loan (w/o proof of income, property DTI, etc).

I’m contemplating setting up an LLC in either CA or TX (series LLC).  

Both myself and my friend are deeply contemplating rental property investment when we turn 18.

I'm currently in the "stack" investing strategy but am contemplating saving up for longer and trying to jump into a bigger deal so any advice is much appreciated! 

However, I am contemplating purchasing a condo until I could increase my savings to try again later. 

I am a little nervous I have been contemplating this for about 3 years and finally doing it!