A quick search seems to come up with companies willing to fill this role for $100+/year.Should I be paying for this service for each LLC I form now and in the future or should I use myself or my spouse?

I also recommend you looking into other creative financing, as this will help you achieve your goals in your desired timeline. 

If not, use a skip trace service.

I got married to my beautiful wife and recently separated from the service.

Some sophisticated lenders are now using the debt service ratio instead of DSCR after 2008.

Dropping the rents $100 a unit would still cash flow $200/door with the tenants paying utilities.Numbers at a glance:Gross Income- 22260Taxes- 2084Insurance- 1000Management- 2226Utilities- 9500NOI- 7450 assuming no vacancy or CAPEX (just to illustrate how bad the current numbers are)Debt Service- 6535 (30yr, 20% down, 5.5%)Annual Cash Flow- 915 (Actual for this year with my debt service is -4797 due to CAPEX and no vacancy).

If you plan to expand your portfolio you may decide you need a PM service. 

Are fellow syndicators aiming to achieve this as an average over the life of the deal or from day one of the deal?

While the HOA has a strong argument using this clause against you, I think you have an equally strong argument that the spirit of that clause was to stop owners from selling products or services out of the home, not to stop STR.

I'm just not sure if the bank/servicer are obliged to bid the market price minus the Net Value cost factor (15.95%) or the balance of the loan.