It depends on the rental income, what you plan on putting down (20-25% is typical, 15% or 25% is required for conventional depending on # of units) For your owner occupied deal, you should be able to use a portion of the rental income to qualify and help offset your DTI a bit. 

Whether you need a CPA with just three rentals depends on the complexity of your situation and your comfort level with DIY tax prep.If things are pretty straightforward, you might be fine with tax software for now.

For my clients, this SCREAMS of building equity, provided the ARVs would support the rehab.

If I had to pay my cleaners on top of the loss income it would impact even more as my cleaning fees range from $100 to $400 depending on the property.  

@Alex Martinez it all depends on your portfolio and the Class of properties-tenants!

I have never provided a water dispenser/ice maker in any of my other units, but rather a Brita and ice trays with no complaints.

Depending on your goals and how you are buying your properties you may notice that certain areas are difficult to cash flow in NH depending on your strategy and what type(s) of properties you are looking at. 

If you are providing champagne or wine, would we need a license for that to do so? 

Depending on the value at the time of death and your basis you may need to file a gift tax return.I would speak with a CA attorney to determine the best type of deed to file and a tax professional to gather more information.

It can depend on the property, but owner paying the bills seems rare these days.