I feel a loss of direction and that makes it really hard for me to focus and build.Do we keep at building a portfolio of small multi family (very abundant in my market, very rare to find anything above a triplex for sale), with plans of selling the portfolio and 1031'ing into larger properties? 

I'd been working and saving for many years, however, did not feel it was enough.

It Just feels that way!!!

Feel free to DM me. 

This could be coupled with the a dramatic drop in the S&P 500 which would feel pretty awful.

The seller is out of state and even visited the project a few times to check on the progress which I think helped him feel good about the whole deal as well. technology made the whole process a lot easier in the interim.

Your ability to close means almost everything and you'll need to make them feel confident in your ability to do so if you target bigger deals right out of the gate.2. 

Kind of silly but I always feel they keep the best deals for themselves

Hi Caleb,Welcome to the Bigger Pockets Forum and if you ever have any quetions feel free to reach out. 

I get the feeling you don't enjoy being a landlord, so I agree that you should consider selling and investing in something that doesn't include tenants and toilets.