All right, I guess I'll drop the on-site handyman idea.

I guess I’m not going to benefit a lot in taxes.

Because the buildings are nice and have 3/2 or 3/3 layouts, I'm guessing tenants stay longer than in 2/1s.

Based on all that you've said in the way of "what ifs", and taking into consideration the following:a - $1000 rent - expenses (guessing 1/3 with no mortgage) ~ $700/month in CFb - CF would then be around $8,000/yearc - If home is worth $160k, and you sold it for $155k, minus closing costs (about 10%), you could walk away with around $140kd - If you kept the property, and the CF/year, it would take you 17.5 years for the CF to equal the Profit if you sold it now.e - If you invested the $140k into 20% down payments for 7 units worth  $100k/ea, and each (financed) property netted you $600/month in CF, you could have an actual income (not gross...net) of over $4k month.

But I guess that’s why tenants are tenants and owners are owners.  

My guess is that at some point you will pass a threshold where you will need a CRM, it's Inevitable.

He wins, you not so much.I guess it really just depends on how you structure it and how he gets compensated.Everybody on your team, and your partners in particular, have to be rowing in the same direction, and that means you all (as in all y'all) need to have a financial interest in making sure it gets done on time and on budget. 

I don't have much experience in the syndication sphere, but if I were to compare to my guess on the makeup of the average REIA meetup:75% have never done a deal, even if they've been attending the meetups for years25% have done one or two deals5% have done more than 2 dealsSo just doing a few deals puts you at the top end of things, and there are generally just a few at each meetup who thoroughly know what they are doing.I'd imagine the multifamily sphere is much the same, since this breakdown seems to hold true in most industries (even outside of real estate).

Or is it better to rent in NY for the two years and start looking for investment properties elsewhere closer to where we want to be investing long term (I guess another downside here is that you can't use a FHA or VA loan)? 

I guess my location wasn’t showing on my profile.