Regarding taxes, I believe LLCs are pass-through entities, and you will just claim the income on your personal tax returns.

My 2 cents is that for non-sleeping areas, hot tubs, pool tables and movie rooms are top amenities that guest have personally told me they like the best.I think an outdoor rated pool table (or maybe ping pong table), TV and comfortable seating would likely be the best bang for your buck.

Do you think if the grant deed showing the transfer from the personal name to the LLC would work? 

The LLC protects your personal assets from liability of your business.

I have a mailing list of over 3000 recipients and are aiming for a personal touch with letters that appear handwritten and are signed in ink.

It's important to do your homework and think about your personal risk tolerance and long-term goals.Good luck!

Thinking about setting up a property management company to use for my rentals to show the income as part of the management company rather than personal finances.

House hacking will also give you some personal "property management" experience.

Accounting firms typically have nothing to do with this process unless somehow the title company subcontracted the preparation of the 8288 to them (which really isn’t necessary as it doesn’t require tax expertise, only familiarity with the FIRPTA procedures in general, which any title co who’s worked with a sale by a foreign person would likely know).This is indeed a weird situation and it definitely is unsupported by any authority in the code and regulations to send the withholding tax amount to an accounting firm acting as a middle man for the IRS unless they somehow expressly made an agreement to do so.Good luck with that

House hacking will also give you some personal "property management" experience.