Every time I am tempted to do exactly as you suggest, something like this comes up where having the ability sames me a ton of time.  

I've ran about 30 properties through the BP rental calculator, even if i renovate the basements I'm always coming up 400-1000 dollars short of breaking even.

Does anyone have recommendations on banks or have a contact I can reach out to set everything up? 

And in this phase simply put, prioritize comfort and convenience in every decision.

I'm thinking of signing up for Pro (mostly for tools / calculators) and also checking out other rental calculators online.

So its good to team up with good people to help you build up a good foundation so you have the best chance of success with people and systems. 

On 1-4 unit transactions some lenders offer up to 85% financing for investment property transactions.  

How much sooner into the future are you going to pick up a second place.

It's up to you whether you want to switch the title into the LLC later, but note that this can also be done through refinancing into a business-purpose financing like a DSCR.

There are lots of ways you could do this, but the execution is largely up to you.Most of the private lenders I have worked with were experienced real estate investors themselves with excess cash they wanted to put to work.