From this you need to take your debt service (1500 - 1700/mth) and set-aside a reserve for Emergencies/CAPEx ($300 - $600/mth).  

We run Call Porter an answering service for investors (and are also buy and hold, wholesale, and flip investors) and get to chat with clients about what is working/not working all the time.

I have raised money, had done creative financing through credit cards at 0% interest rate, relationships with Hardmoney lenders, and have just started my pursuit with corporate credit andBig lines of credit.

Mind you we only raise our tenants roughly $20-$25 a year.

They are full service and do property cleanups with their list of go-to subs at a 10% management on renovations.

The insurance policy raises from 1200 a year to 1800...

Generally I use other companies that provide the service because you more easily tailor the type criteria you are looking for. 

A couple of the lease rates are below market rent/sq ft, so while I'd like to bump those up a small amount as they've never been raised, I also don't want to immediately have a bad reputation with those tenants.Suggestions or past experiences?

I think buying is a solid choice as long as you make some good contacts while your hear, most importantly a good property manager but also try to find a good handyman for service calls, a good cleaner, good yard person, ect.  

I had a tenant who begged me not to raise rent for YEARS.