I am an experienced real estate investor, but had never operated as a loan agent before.

As an agent, this is how I typically operate as well.

I've used Thumbtack and found loads of good subs.

You have to subtract the original $230k you paid out of pocket first...which leaves you with $715k.Now, subtract all the lost income (now negative CF) from the months that you had vacancies, Maint. costs, CAPEX, etc...assuming 15% of rent per year, that's about $15k x 15 years = $180k...which leaves you with $535k in virtual profit.IF we just stopped there, you would have gotten $35k/year return (on average).Now, comes the big money losses.You will be operating at an average loss (and this is real money due to cash out of pocket to pay for expenses not covered from rent due to now negative cash flow)  per year of at least $15k.If you had invested those losses (and since the source would have been liquid this is not a virtual thing) at a measly 5% per year, and reinvested it all every year, you'd be at almost $800k in actual real money.Anytime you accept hard cash losses, you are losing the benefit of your cash being a "verb" instead of a "noun"...and you lose all the compounded profit from you cash being reinvested and in action...forward action.

Apparently he is still operating in some markets.

Where operators get into trouble in larger MF is lavish assumptions going in, placing the wrong debt on the deal, and not stress testing the deal/market. 

Insurance is expensive in Fl. and higher for companies if you operate as an LLC or S Corp like me.

Hi BP, I'm Director of Operations for a STR Management company managing 90+ properties in the South.

I know nothing about mortgages and I’d like to find a place where I can learn the terms and all the little operating parts of getting financing and the actual purchase of the house/closing. 

@Matt Dabek Been in this situation dozens of times for clients and my personal investing here in Connecticut in what is probably the same market you operate in.