If you know of any service providers who can write and prepare these letters, possibly on the mainland, and then ship them to me for a final local dispatch, I would greatly appreciate your recommendations.

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

Nick,I recommend "Certified Tax Coaches" and "Certified Tax Planners".Do an internet search for those designations "near me".They have tax-saving strategies that most tax preparers have never even heard of.PLUS they specialize in real estate.Good Luck!

This entails building personal/working relationships with people successful in the field.

If you buy in the right community and prepare your house to be as unique and memorable as you can, you will (should) do very well.

We were prepared to do a land contract with them and had all the papers signed through a real estate lawyer. 

I hired a broker to help me process the application and prepare a lease.

Likely you should be prepared to absorb a moderate jump in your policy costs, as that seems to be the norm in the current market that I'm hearing from other clients as well as a broker/investor/prop. manager myself. 

Additionally, evaluating your finances, searching for properties that meet Section 8 requirements, negotiating with sellers, preparing for Section 8 inspections, applying for Section 8 approval, and effectively managing your property are all crucial steps.

This entails financing and various local laws and whatnot all converging for universal agreement, so herding cat's.