Specifically, I am interested in learning more about syndications, working with lenders, lawyers, CPAs, and other professionals involved in cross-border real estate deals.

Crossing my fingers that this would be possible.

Based on how I am reading your summary it sounds like there is solid equity in the 2-family in order for a bank to cross-collaterize assets. 

I recommend waiting until your unit count is higher.  

In my experience many unlicensed wholesalers operate in a grey area and often cross over into what is obviously brokering real estate without a license. 

@Khaled SeirafiRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Bridge Loans or Mezzanine FinancingShort-term financing can cover the down payment:✅ Private lenders: High-interest, but great for acquisitions✅ Mezzanine loans: Secondary financing sitting behind a primary loan✅ Cross-collateralization: Leverage equity in your existing motel or rentals4.

Obviously the answer is yes when it comes down to the cash flow, but I am particularly wondering if HCOL/high property tax areas are places you would cross off the list entirely.

They can help you cross-check your estimates.It’s always better to overestimate expenses than to underestimate and face a shortfall later.

Most voucher recipients only look at the bedroom count when making their inquiries.