Self management works if you are local and can separate emotion from business.

I would anticipate it would depend on the level of detail you desired but it has been my experience that the will do free estimates.

Don't quote me on that, but it's easy to look up the IRS regulations.I recently had a conversation with somebody else who is planning to start an STR business. 

The management companies & local investors usually lease places up within 1-2 weeks max (depending on if you want to hold out of higher rents) How would you think about leasing these out? 

I would avoid this business model.

Give your state's 'cure' term ("In New Jersey, a tenant has three business days to pay rent and court costs after a judgment of possession is issued to avoid eviction.

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

Most businesses, property management or not, fail due to the lack of sales, not due to the lack of systems and phone etiquette.

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 specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your accountant remotely to expand your options.I would also recommend looking for an accountant willing to work with you throughout the year.

Will depend on several factors like the type of property, type of tenants, your risk tolerance, other assets you own, your estate planning, laws where the property is located, etc.