If you are setting aside funds for capex, taxes, insurance, or other expenses that don't occur monthly, transfer those funds to Savings each month and hold them there until it's time to spend them.

The fact that you’re here shows that you’re serious about learning and growing, and that’s half the battle.If you’re looking for real, practical guidance, I’m happy to help.

Specifically:Will the lender only consider the rental income from the two legally zoned units, even though all three rental incomes are declared on your tax return?

I'd advise you to dive deep into the forums, there's plenty to learn! 

You get to harvest the equity tax free.

This approach would allow me to learn with each deal and minimize initial risks.2️⃣ Go Straight to Multifamily: Instead of starting with SFHs, I could spend time learning the multifamily business and go directly for a 20+ unit building, maximizing scalability from the start.I have no experience with either strategy.If you were in my position, which strategy would you choose and why?

If you're just going in to learn, you could probably gain some value.

I started my jouney here in 2011 and I am still learning everyday - especially from others on this forum.My personal portfolio is located within Stamford and Bridgeport.

Buying a portfolio without experience just throws you in the deep end without the ability to learn and develop these things. 2.

Rentals generate passive income, so an S-Corp offers no added tax benefit.