On the flip side, rather than buying the nicest house on the block at our destination we’ve decided to downsize from 2900 sq ft, 4 bed/2.5 bath, loft, den and a pool to an 1100 sq ft, 3bed/2 bath cozy home with a small backyard (no more yard work!). 

Tenant cut off all communication (blocked my number), Minimal personal stuff remaining in home (~$300) and some foodShould (can) I Re-rent?

It makes economic sense but where I am running into my “mental block” if you will, is this would be my first deal ever and am kind of in a state of paralysis since I don’t know if this is something I should go all in for and just do it or try and find a partner to help handle it.

The owners had a sale lined up but it was stopped by an injunction from legal aid blocking the sale until the lawsuit is settled. 

They either want it or they don't.The 50 or so units that I own that are closest to the stadium and Five Points (bar district) are much easier to rent than better, nicer houses that are even just a 5-10 blocks away.

I own a couple of places within a few blocks of there though, and am curious if I'm underpricing.Long term price appreciation potential is huge though

When I bought my brand new block 1910 sqft 4/2 house in 2009 for $180k, I looked around in the nicer areas of Altamonte Springs that I knew from my childhood. 

I have the junkiest house on a block of million dollar, San Diego bay and downtown view, hillside homes.  

I recently signed a contract for 800k to buy 4 units a couple blocks away (I like to have my units close together).

Several bidders using online mapping were feverously bidding on the property.At another sale a 3 story brick row house looked good from the front, but to see the back you had to go all the way roaund the block to access an alley to see that the entire rear wall had collapsed into the back yard and there was no rear wall to the house.