I use licensed vendors who specialize in their trades (HVAC, plumbing, electrical, pool, etc.), and it’s worked really well for us.

If you do not like bookkeeping/accounting/technology, hire a bookkeeper specializing in real estate investors. 

They specialize in hard money loans specifically for real estate. 

Because the condo price is so low, I would still have a decent monthly savings rate towards my next deal.I’ve done a lot of research on duplex house hacking but almost none on condos, so I’m unsure how big of a deal things like HOA reserves, rental restrictions, special assessments, or resale value are.

I'll look more into hybrid/segmented special assessments.You'd think lenders would be mostly okay with these, since while it's true that only a portion of the units are responsible for repayment, the loan amount itself (their risk/skin in the game) is lowered by the same factor (slashed in half in my case).I know this is silly and I probably won't go down that route, but part of me is thinking, "I'll be the lender myself - I'll give them a less predatory (but still win-win) interest rate - if anyone has to collect interest here, why not it be me?"

Mortgage brokers who specialize in DSCR loans can be helpful since they have relationships with DSCR lenders.

@Jason Harrelll - I've bought directly from owners on multiple occasions using seller financing, subject-too and lease-options.

As far as the process goes, it starts with having a good lender that actually consistently specializes in reno lending. 

Best note flow for me comes from relationships first, lists second: I work direct with smaller banks/credit unions’ special assets, property managers and loan officers who flag nonperforming borrowers, and active investors offloading re-performing paper; I’ll also tap a few vetted brokers, but I require full tapes, collateral files, clean chain of title, and recent pay history before bidding.

@Jason Marcordes do you guys handle this in any special way?