Why do they automatically get thrown into section 8?

Brick v.s siding and covered v.s no converted parking also make a large difference and are items that have to be adjusted for. 

That’s not a risk adjusted return close to what it was.)

The renovations were already factored into the LTV during the initial loan approval, and the increased value of the property due to those renovations may not automatically allow for an earlier PMI removal under Fannie Mae's standard policy.Workaround/Next Steps:Reappraisal: You might be able to request a reappraisal if the lender is open to it.

If things are tight right now, maybe consider a side hustle or extra job until rent adjustments give you more breathing room.

Listing it “as is” with a $25k rehab concession can attract these buyers.Consider these options:List on investor-focused platforms like Roofstock or BiggerPockets or Facebook Marketplaces, where you’ll find buyers who appreciate tenant-occupied properties.Network with local investors or REI groups in your area to find someone looking for a turnkey rental with upside potential.Hire a real estate agent experienced in selling tenant-occupied properties, but adjust your pricing to cover commissions if needed.Make sure to highlight the stable tenants and ADU potential—those could be big selling points!

I love how Mint was "semi-automatic", and did a decent job on its own although you needed to come in and tweak categories.All this to say, are there any other Mom & Pop investors out there with more complex personal finance that have found useful software solutions? 

Compare that to the seller's staffing matrix and make adjustments as needed. 

Constantly manage bookkeeping and cash flow to make sure you stay on budget and/or make adjustments when (not if) things come up to stay on track.  

if you add one ADU, you will likely be comped against quads with maybe a slight adjustment for it not being a true quad.