I would like to know how I can calculate my "Gross Annual Income". 

Return is of course highly dependent on how much you purchase the property for but if you're talking strictly gross rents, there is plenty of opportunity in this market.

The lender will use 75% of the gross rents from property #1 towards your DTI. 

Based on my evaluation of the property the gross rents will cover all expenses (PITI for traditional loan and HELOC); therefore no money down purchase.  

A unit that experiences just an 8% vacancy rate (1 month) under management will barely break even unless it's cash owned; 2 months is negative for the year most likely, as you are then at about 20% gross rent for management.

Giving us a total Gross rents of $3030 with PITI of $1250.Lessons learned?

For background info: Our tenants are paying approx $11/sqft/yr gross leases now which should be at $13.5 as we sign new tenants.

We're getting $1500/mo in gross rent, about $1300 net, so less that the desirable 1-2%. 

Does the 1099 show gross income?

So if I'm renting a unit for $1100 a month should the tenants monthly income of at least $3300 be their gross or net monthly income?