The plan was to fix up that house an rent it out long term but with the market being high and I was moving out of the area it made more sense to sell at time. 

Baseboards, couch cushions, above fridge, in cabinets, grout/caulk lines, rug maintenance, air filters, windows inside and out, dust the top corners of windows, corners of high places etc etc.  

Got to take the lows with the highs.

I know I just ratified a transaction where I was selling a new build ( not yet built) and the broker representing the buyer had a very high buyers broker agreement that simply does not work for builders and what we have to do to manage the process.

In Detroit, for example, I like to focus on strong C-class areas where Section 8 demand is high, but I still get some quality control over tenants.What’s the process like for becoming a Section 8 landlord?

So i have pretty sizable personal assets, along with a relative high income. 

You are asked to assist our pest control by maintaining a high standard of good housekeeping.

With the high housing market in the past few years, house-hacking and living "rent free" is very tough almost everywhere in the country, especially if you are planning on putting <20% down (higher mortgage payments + PMI).

Assuming it will be Single Member LLC (you as a member/manager), it will come back on your schedule E anyway, so only thing you loose is $800 in california and bit more of paperwork but that preps you for future.Note - this is a very high level advise and mostly a personal preference. 

With regard to your "DST" and as with many highly structured tax vehicles that have a potential "self dealing" quality to them, there are a number of potential potholes you can easily step in along the way (e.g., constructive receipt doctrine, effective control over nominal 3rd party relationships, lack of genuine risk bearing and compliance with transactional terms, etc.).