Automating check in, weekly rent payments and checkouts will be a huge step for us.

@Tim Swierczek Thanks for the information, I will check it out.

I would also check median home prices vs. rent potential, landlord-friendly laws, and supply vs. demand trends.

I will definitely check out the CREIA!

deposited in a demand deposit account?  

@Jacob HavlovickBigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.

As a result, no MiniStays account for me. 

So we create a partnership agreement and a new LLC and he funds the LLC account with 50k.

Always good to check before you cash out the 30-35k, which I honestly would not do with the drastic change in PITI, numbers would be tight even if you rent out the unit you are currently staying in.