So in that sense you've got plenty of time - both to set up the 1031 and to continue your due diligence for your replacement properties.And although it may feel daunting you've done a fantastic job of distilling down the questions. 

My criteria for buying are at least a 10% CoC return, and $100/month or more in net cash flow PER door (hopefully closer to $200/door).List Price:  $179,900Down Payment:  $44,975  (25% down, assuming I buy at list price)Repair Estimate:  $5,000Closing Costs:  $2,500TOTAL CASH IN:  $52,475Loan Amount:  $134,925Loan Terms:  5.25% fixed rate, 30-year mortgageMonthly P&I:  $745Monthly Rents:  $2,000 ($1,000 per side)Vacancy Loss:  $100/month (I estimate 5 - 8% on multi-family properties, depending on how popular the area is).TOTAL MONTHLY INCOME:  $1,900 ($2,000 - $100 in vacancy)Taxes:  $154/month (you can usually find the actual tax amount paid for the previous year on your city's website)Insurance:  $100/month (ask other investors in your area what they pay, or for recommended agents who can give you quotes)Water/Trash:  $80/month (this is typically paid by the landlord in my area)Sewer:  $50/month (also typically paid by the landlord in my area)Lawn/Exterior Maintenance:  $75/month (my property management company offers this service)Maintenance:  $100/month (people budget anywhere from 2 - 10% for this... if it's a well updated and maintained property in an area that attract responsible tenants, I budget on the low side)Property Management:  $100/month (usually 8 - 10%, but you can find PM companies that do it for less... just make sure they're good at what they do!).

I think if you have "boots on the ground" in place in NY and/or don't mind making the trip then you should take advantage of your knowledge of the local market.I am not sure where you are getting your list of apartment owners from, but I typically use a cheap postcard on my first mailer to "scrub the list". 

Maybe in a nutshell the typical process, chances of actually winning a bid?

They typically do not go ( they are with such and such company so I will go with them.) 

There are no repairs requested, no loan contingency, no appraisal contingency. typically no cold feet buyers who back out for no good reason, etc. 

For a cash out refi, typically your LTV will be 70% on a multifamily, so you would need it to appraise for $1M in order to pull out $700,000.

I typically ask about replacement dates of roof, electric box, plumbing and water heater).

As noted earlier the depreciation recapture isn't typically eligible for instalment sale reporting benefits. 

Also realize that typically (or recently in my experience) banks are tightening up their apprasials.