I have RentRedi charge them a late fee after the 4th day if rent is not paid.

Quote from @Briley Roe:  yes those fees are very high as you have a broker fee and other fees for a loan little over $100k at 6+ points. 

Property management fees and software subscriptions are deductible, and depreciation reduces taxable rental income.This post does not create a CPA-Client relationship.

We then lease the property on a 3-year lease with the option to buy and the tenant buyer gives us a $4000 option fee to buy the property for $260,000 within the next 3 years.

Buy and renovate the property and in 6 months do a simple cash out refinance and pull out some cash and start the REI process all over again.I am North of you up in Pinellas County West of Tampa and there are also some great places up here that might save you some cash. 

For now, it Looks like your roommate/tenant can cover half of your mortgage (plus hoa fees). 

I use Buildium for tracking rent, fees, leases, and collecting online payments, but I don't use their reports for much, as I end up copying my online banking each year into spreadsheets.I've been using Rental Hero for the last hour and already impressed with it.

This requires consistent oversight and experience, which most investors simply don’t have.The Bottom LineIf you want to lose money and risk expensive legal fees, go ahead and self-manage.

What I am looking to do is refinance, or pull out equity so I can get back on track with my lender and continue searching for a buyer. 

If the property sold today, after 1% cost of sale there's only $2.5 million in cash coming from that sale and that's assuming that there's no exit fee on the loan and no outstanding payables.