Not to mention they have a dozen other agents just like you busting their tail for them. 

Assuming the insurance premiums don’t significantly impact my cash flow (which is one of my primary goals), how do you assess the risk of taking out a loan under my personal name versus opting for a commercial loan that requires a larger down payment and comes with a higher interest rate?

From my experience (being on the DNC list and getting dozens of telemarketing calls a week) the main strategy is to ignore it and call everyone anyway. 

He can try to work out a modification of the loan in some way, and there are literally dozens of different types of modification that may be appropriate for any given situation and may prove beneficial for both parties.  

It is quite common to conduct a move-out assessment for damages and apply the costs against the security deposit (SD).

I think they got rocked in FL and the southeast generally are still assessing things.

By sending a check, in many states, if the tenant cashes the check they are de facto agreeing with your damage assessment and will have little ground to dispute your accounting.  

The call has gone out dozens of times for anyone on BP to tell a story about how having an LLC saved them.

Visit their office (or request a virtual tour) to assess professionalism.

The only thing is the HOA fees go up and they can do special assessments and you have no control over it.