Frustration with current market: Seeking wisdom, encouragement, lend me your tenacity

[Logan Jamieson]

First off, let me start by saying I logically understand a winers attitude is not based in victim mentality.  I also understand there are deals anywhere at anytime.  

That being said...  I find myself consumed with anger and frustration.  I have worked really hard over the past decade to position myself to begin to build my portfolio.  Since 2020 I have doubled my salary, moved into an apartment with my father to save rent, and was able to save over $150k cash towards an investment.  

I have never owned my own property, yet grew up in a family real-estate holding company and directly understand the power of real estate investing.

Since 2020 ive seen homes double in price.  Ive seen rates go from <3% to >7%.  A $300,000 house in 2020 at 2.9% is like a $1,200 mortgage.  Double the cost of that house and double the rate to 7% and its like $4,000 per month for the EXACT SAME HOME.  I feel like im going crazy.  

I did most everything I was supposed to do, increase my income, decrease my living expenses, save cash, etc..  The thing I did not do was ENTER THE MARKET, and am now filled with regret.  

Questions:

1) Whats the lesson here? Is it that I should have entered the market and therefore should enter now? How do you all make the numbers work? I like the idea of BRRRR but struggle to see how it works in this market.

2) How do you all deal with regret and resentment?

3) Am I crazy to feel this way?  I feel like I am living in bizarro world and honestly dont see anything changing in the near future.  Am I wrong?

4) Id like to invest where I want to live, since I need a place to live.  My places of interest are: Rochester, NY.  Southern Maine (Near portland), Research Triangle, NC, and Jax/ St. Aug., FL