There is no timetable anyone can really give you.

Given enough time, tables will turn {again} and real estate elsewhere - perhaps even in Canada - will provide more opportunity than the U.S.A.

Learning the ropes in those trenches will help you carve out your niche to manage your time tables and expense levels.  

Do they both become part of basis of property or do I amortize or expense either item on a different timetable since the unit was technically ready and available for rent when he saw it on October 25?

Tax qualification may be at risk of being lost.Excess funds need to be redistributed to members in an HOA if there are excess funds that can not be justified, they over collected for expenses.I'd say 100K among 32 members for a 1/2 mile of road is justifiable, in fact it could be a little low depending on road conditions.They need to address the road condition and the expected expense and time table for repairs to invest or keep these funds.

It really depends on your time table and how much cash you have in the bank.

As for option 2, using the garage example,I imagined that I would create 2 lines on the form 4562 for the same physical asset, but that each line item would have its own 'date placed in service' and each would be placed at 100% 'investment' use percentage, and each would depreciate independently of one another, each on its own time table (i.e., both at 27.5 years, but that each asset was placed in service at different times).

They are most likely looking to buy the note as a means to ultimately acquire the property via FC or a DIL.In addition, they will also have an idea of what it costs to see a FC all the way through, as the time table and costs vary from county to county.

Agreed unlikely to find a better property at this point in time, just was most curious for input on the timetable in general

If you don't tell them, your messing with their dreams and their timetable.