For STRs... what's the best way to gather the data on utilities, pest control, pool cleaning, general maintenance, etc...?

Expensesget taxes from county. look at current valuation and you should have a good guess at how much it will go up based on purchase price.Find out what expenses are paid by LLVerify which utilities are separately metered; get average winter/summer monthly costs from utility company for any 'house' accountsGet quote per door from your insurance agentGet a quote from your landscaper (find out what they pay)Get a dumpster quote if you don't have city trash binsFind out if there is a parking lot sewer feeFind out rental registration requirements and costs (can be both county and muni)Income:Get the rent roll, In the contract require that you get estoppels signed by tenants and current owner saying amount of current rent, security deposit held, past due balances, and spelling out any promises for additional work/upgrades (there shouldn't be any). 

People also forget that even if you pay cash for a home you still have insurance, utilities and taxes.

@Justin Sullivan Lets flip this - how would you feel if your utility company kept charging you $50 for a service you no longer receive? 

So as you can see he has been living there without paying a dime for close to 2 years (and not paying the utility bills either)  We had intended to go the eviction route but gave him three options 1) Vacate the property within 30 days and when we have access and a vacant house, we would pay him $2,000 (Cash for Keys)2) Buy the property from us and close in 30 days ($10K over what we paid)3) Go through the eviction processWe have him three days to make a decision as to which option he wanted to pursue and he indicated he was trying to find the money. 

Preferably, units would have separate meters for utilities to be paid by each tenant. 

I'll have a bit more money that I can then use to invest in other properties; hence being able to utilize all the tools BP pro has to offer.

I also have a landlord account with the utility companies so I made sure to have it default into my name once tenants left.

You start getting into roof, structure, parking lot, utility lines, etc. it acts almost like a gross lease even though called a NN.

Once it's done, I have a partner to bring into the company and then we will need figure out our crystal clear criteria and where we want to take the company and how we will best be positioned to utilize OPM for future opportunities...On the coffee side, I really want to figure out a good metro area for a test.