I think if most flippers are honest (10-years later looking back), they'd prefer to still own those homes as cash-flow positive rentals.I don't remember where I heard it (so I'll attribute it to MLK or Abraham Lincoln, maybe Warren Buffet) - "You can get rich flipping houses, but you get wealthy keeping them as rentals".

A couple years later, I bought another and fixed it up and got it rented.

As the area appreciates, they would hopefully be able to refinance to better terms from a bank at a later time and you could recoup your investment and hopefully capitalize on some profits.

I’m thinking bigger is better vs 1 bedroom but won’t be able to test that until later this year  

We’ll chat later.

I have a call with a real estate focused cpa firm later today.

If they are not going to sign it up front, then they aren't motivated enough to sell most likely, and it might be a good idea to move on and try another seller lead and/or come back to them later when they are more motivated.

Further more, do I need to find some professional to help 3 years later to keep the tax low?

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

So it's more of a "pay me now or pay me later" thing and either is actually fine as long as you plan for it.