Seems like there are several ways to approach this market, but I believe making "Aggressive" offers that are in line with the upcoming housing correction can allow you to be ahead of the curve when that drop actually happens.

At your age, you've got decades ahead of you, and decades for whatever you buy to appreciate.

Good tenant, good area, compensated fairly for them breaking lease plus you saying you wouldn't hold them and them communicating with you ahead of time I would let them go.

At least, I'll be coming out ahead. 

Your agent should be getting advance notice of properties “coming soon” to the market, so you can get a head start on analyzing them. 

From what I can tell from your picture you have decades of investing ahead of you.

Sounds like if I were to go ahead and invest in a larger multi-unit I need to prioritize setting up a solid team and ensuring I have plenty of reserves before engaging.

Therefore, im getting into a place thinking is it because of the holiday season or i should just go ahead and less my rent.

All of this is subject to what lies ahead.

Ahead of that,  read Section 4 in the link to the real estate CPA.