Wholesalers literally exist to find those off-market deals.

The existing mortgage is still in my personal name, which I’m not thrilled about in the long term. 

The right solution depends on the specific layout, travel distances, stair enclosure and rating, window size and sill height, and how the jurisdiction applies IBC and the NYS code for an additional dwelling unit in an existing building.Whether it is worth it comes down to a simple feasibility and ROI check, the all in cost and timeline to legalize, versus the increase in stabilized rent and appraised value.

Buy with seller financing with sweetheart terms ( assumable, 0% interest rate Seller Financed Note) and sell wrap note higher interest and or higher price for providing financing to buyers who would not qualify for conventional loansSell a property with an existing low interest mortgage utilizing a mortgage wrap.

Ask the existing tenants what room renovaton would they:1) Pay an increase in rent for2) Not mind that it be done while they live there;or if they can stay with a friend/family for x days;or if they're planning on leaving for a vacation anytime in the near future when they work can be done

This actually adds you to the vendors insurance policy, whereas an insurance certificate only provides proof that coverage exists.

Infill lots, minor subdivisions, or land with existing frontage and utilities will teach you more than any underwriting model.Also worth noting: lenders and equity partners don’t underwrite first-time developers on vision.

You can also ask the seller for only what already exists, framed as a quick handoff rather than a demand.

From a numbers perspective, this looks pretty solid, but it really comes down to what you’re most comfortable with.With 20% down, you’re in a good position to either pay off or significantly reduce your existing balance, which lowers your risk.

They can help you stay out of trouble you didn't know existed, and also stay focused on the aspects if your business that actually interest you.From the title of your post I see you are located in Ashburn.