When I hit around 1,500-1,600 sf, it becomes more favorable to do the mod.

That was until it was time for her to move, I had decided to sell b/c the market was in my favor.

Explore FHA or conventional loans based on your eligibility and current market rates.For a medium/longer term strategy, keep an eye on interest rates for potential refinancing opportunities for Property 2 when rates are more favorable. 

There are too many ways to manipulate the numbers for them to work in your favor. 

Since investors and househackers in New York are exposed to more inventory, they are seeing dozens of available properties that fit their criteria vs. just 1-2 properties a year ago.We have more available options, which results in househack investors and homebuyers having more time to negotiate lower purchase prices, better terms, and more favorable contingencies.

I normally end up going with a small bank that provides favorable terms for holding my cash.

They're nice guys so they are very unlikely to ignore you (I won't say certainly because I don't want to volunteer their time and attention for them - but the odds are certainly in your favor.

Efficient negotiations secured the property for $158,000 on favorable terms.

Through efficient negotiations, we secured the property for $196,000 on favorable terms.

It’s not the RE making the money ( other than buying/ building at favorable pricing).