Unknown = risk.

But given the cyclic nature of the real estate market, as well as unknowns as to what the current administration might do to influence housing affordability,  you can really ever know what will come next.  

Even though I'd remodeled 9 units prior, doing a remodel at this scale has so many more unknowns with the code that it's tough to budget accurately when you're stretching far beyond your current knowledge.

That's it  I'd love to get into multi-fam, I think, and eventually commercial, I think, but lots of unknowns at this point.How involved?

If I am reading your numbers correctly you are saying that you are cash flowing $876 annually for a $53,000 investment plus your time, risks and unknown expenses e.g. loss due to vacancy, cleaning after a tenant destroys the property, painting, carpets, utilities when it is vacant, new water heater, furnace, air conditioner, leak in the roof, broken or leaking drain pipe, sewer, water pipe, gas leak, or replace or repair leaking faucets, broken screens, repairing locks, trash removal, city sewer use fees and a lot more. 

You need to hit a 20%+ spread on ARV after all costs just to account for the unknowns that always show up mid-rehab.Best performers right now are neighborhoods in the 35th-45th percentile price point, not the ultra-hot coastal areas or the super-affordable inland stuff.

I'm being conservative with my assumptions to account for all the unknowns, but I'm also worried I'm overanalyzing each deal and won't be able to find anything cash-flowing.

Either scenario is unacceptable.Had we not actively managed the management company ourselves, we estimate we would have lost over $3,000, in addition to having unknown individuals occupying our home.Homebase charges 20% of rental income, which is a substantial fee.

I work with many investors, and have done myself, who are looking to get rid of the continuous unknown of maintenance fees and get into a new property that needs no capital improvement for over 10 years. 

Good cold outbound requires getting around the mental "sales filter" that we all screen calls from unknown numbers through.