I'll be sure to keep all your advice in mind as I look for my first house hack! 

Housing does annual checks and the units are usually kept well. 

Doing MTR inside of your own house is not something I think trends that well.

@Megan Mason recommend you watch some of the videos from @James Wise youtube channel on S8 evictions.We've been dealing with S8 tenants for over 20 years and they are NOT a cure-all for rent collection challenges.Since rents in Class A & B areas exceed S8 limits, most of your S8 rentals are going to be in Class C/D areas. 

Has anyone worked with Itel housing?

Hey Ed - this one wouldn't qualify with DSCR if one of the houses is your primary (assuming all are on the same tax parcel).

I don't want to waste your money on inspection, option money, and appraisal money, just to find out the house doesn't qualify for FHA, so I do my best to keep you out of those situations. 

Next, I'll be pivoting into subsidized housing investment and collecting rent $ from the government as i truly do believe this is a way to boost CoC return percentages in today's market.

Even if you only averaged 2.8% appreciation annually, which if you've had it 20 years I have no clue how that's true given prices have well more than doubled in that time, youre skipping over the fact that you have been benefiting from that appreciation on the ENTIRE house, not just the % you paid for.  

Vincent de Paul challenge program and are looking for housing that's willing to work with the program.