Leases generally run first to last of month so unless you have a very special circumstance a tenant can not simply postpone a move by a single week.

As for investing, I'm looking to try to get some passive/supplemental income, hopefully to replace or reduce the money I need to make as lawyer, which is as you know a tremendous amount of work.  

Looking for a broker or loan officer that specializes in Real Estate that you guys have worked with.

They talked about the following method for those who don't want to be super active in real estate:Buy one house a year, ensure rent covers all expenses at a minimum Have each house on a 15 or 20 year noteOnce you hit year 16 or 21 (whatever you amortize the loan for), start doing cash out refinancesThis method only requires one house (more would work too) a year, and would greatly supplement or even provide a retirement.  

There may be other uses allowed, and sometimes a use is a "special permit" use.

Residential loans generally offer more favorable terms than commercial, that's why don't usually hear about commercial loans on 1-4 units outside of special circumstances.Consider looking into FHA 203k loans, or obtaining hard/private money for the construction then refinancing back into a traditional 30 year resi loan after stabilization.

I am looking for a local tax accountant who specializes in real estate investing and preferably owns properties him/herself.

It's best to find one of these outfits that specialize in helping real estate investors.

Are there any management companies that specialize in short term rentals (google wasn't much help)?

If you are supplementing properties with money from your w2 job and that goes away you will feel some serious pain.