How much your place should be renting for specifically...  

I bought a condo in Lincoln Park, it is rented, but I already don't like dealing with an HOA, lol! 

Most lenders are fine with just seeing a signed lease and receipt of the first month's rent with security deposit, so the tenant doesn't need to actually be moved in yet. or 80% though it will certainly make the process smoother if you have a tenant lined up.

Putting it as a long term rental will not give me any cashflow, I can probably rent it out for $1500 max and my mortgage payment is around $2381/month. 

If you think this property will continue to appreciate and the rents will continue to grow, then I'd suggest the cash out refi.

We're pretty conservative with our numbers, so we set vacancy at 1 month rent lost every 12 months, or 8.33% of gross rents.

It has a main house and a back house that is currently being rented.

Over the year, I fixed some items up and raised rents as 3 out of 4 units were under market.

However, I do think if you can hold out for 1-3 years you might see rates drop a bit and insurance drop a bit, and I feel pretty confident we'll start seeing 3%+ organic rent growth per year in the next 2-4 years again.

I don't have much, it's just my owner occupied 3bd 2bth SFH renting out two rooms generating a total income of 1400/mo.