Talk to neighbors (landlords and tenants) to find out what they pay/charge for rent, utilities, pet fees, etc..Talk with utilities to get last year or 2 of actual expenses.  

If we are able, I'd love to use a 5% conventional loan on next property (Owner-occ), since conventional MI can be less expensive than FHA PMI.

Do not over or under report expenses in hopes of getting a loan.Second - If your broker is not willing to find a lender who will count the rental income - you should find another broker or to call up lenders yourself.

Hi - From what I've been reading there are restrictions on HELOC interest expense deductions. 

If you've got multiple properties, do this full time, manage your own and generally run it like a business (ie, you take deductions for meals, mileage, phone, internet, etc.... beyond just "investment" expenses), then I'd argue that you're running it as a business and should 1099.But really, when in doubt, 1099. 

Too expensive haha

Is there an alternative, less expensive way to go about this--maybe a website with RE contract templates and the like?

And don't be too surprised if it ends up being a little expensive, as well as with the insurance carrier that insured Beyonce's rear...

Value 1.3 MillionObvious expenses Taxes, Insurance,  allocating 12% to maintenance.

Going from $690 to $1000 may cause them to leave, which could impact you via vacancy expenses if those units aren't capable of demanding $1000.