House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

What fees to charge and returns to target? 

In my experience apt. conversions from single family are more prone to noise transmission. 

I’ve realized I need additional help—someone local, like an assistant.Here’s my idea: I was thinking of purchasing a small piece of property and putting something modest on it, like a single-wide home or a similar small structure.

.- Value-Add Investments: Beyond cosmetic upgrades, think about adding amenities like solar panels, EV charging stations, or smart home tech.

Your journey from managing single-family homes to co-founding Elevate Commercial Investment Group to assist passive investors is both inspiring and instructive. 

•For your next purchase, check if you can leverage FHA financing again—it’s one of the most powerful ways to scale quickly.Resources to Learn More•Due on Sale Clause & LLC Transfers: Nolo.com•FHA Loan Rules for Multiple Properties: HUD Handbook 4000.1•Scaling from Single-Family to Multi-Family Investing: “The House Hacking Strategy” by Craig CurelopHope this helps!

The cost of a sewer line is the same whether it is on a triplex or a single family home, but with a MFU you can spread the risk.

Going back to the OP, I'm not sure what fees NY charges for LLCs and how many properties or businesses he has but I think these "asset protection" companies overcharge people. 

.- Cities like Toronto will levy another tax (Vacant Home tax) equivalent to 1% of the current assessed value of the property if the property is not occupied (rented, owner-occupied, family occupied, all count as occupied)- Land Transfer Tax: while the Province of Ontario charges anywhere between 0.5 - 2% of Land Transfer Tax when your transaction closes, you should expect to pay this amount twice if the property is in the City of Toronto .