He's putting a lot of trust in me, so I want to be sure his capital is fully his at all stages. 

One is passing on wrong side of road and couple others are excess speeding and all have court criminal infractions coming up. 

Airbnb estimates ~1600/mo average, and I think it is a bit conservative given the location next to public transportation, "coolness" of the unit (100+ year old building that will stage and photograph well), and relatively underwhelming alternative Airbnb and hotel options.Furnishing everything is my biggest unknown that I'm working on, but I would greatly appreciate hearing about any red flags/concerns/oversights that jumped out at you while reading this.

You could end up with a distribution in excess of basis; however, there is not enough information here to determine that.

I think depending on how far you are away from your properties and if you are in the beginning stages and it's manageable from a time standpoint it makes sense to do it yourself. 

You may wish to confirm that the new 401k provider will handle the ongoing compliance support such as any required 5500 filing (e.g. 5500-ez for a one-participant plan with assets in excess of $250,000), any required tax reporting (e.g. 1099-r in the event of a distribution or in-plan Roth conversion), mandatory plan updates and amendments, etc.4.

At this stage you need to be looking at value add long term.

Far too many get stuck in the "paralysis by analysis" stage, thinking they just don't know enough to get started.

Hi @Cody Richard and @Jazmine Bryant I too am in the beginning stages of real estate investing and would love to be a part of an accountability group!

Right now, the next property will be my 10th FHA loan, and I will need to secure financing elsewhere going forward, which is why i have paused at this stage to make sure I have my entities in order.