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.

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. 

Re: off season, I use the old tried-and-true of lowering your price :p  I typically set mine at/near the lowest I'm willing to accept and take what I get (I don't go too low because after a certain point the risk/reward doesn't pay off).  

You are not obligated to accept rent.

Do I want to build a working relationship and transition into bigger deals down the road and use these smaller ones to test out the waters?

A PM will operate your business as it should be run, all you need to do is manage him.Landlords need to understand and accept that they are hurting their business and other tenants when they allow personal feelings to interfere with business decisions.

The first month, I tried to have them use Venmo, but they couldn’t figure it out, so I had to drive out to the property and accept cash.

., even though the California Association of Realtors form is generic in some regards, it is a time-tested, updated, California-specific lease agreement with the backing of a statewide organization focused on real estate. 

The last time I needed a tenant nothing worked accept a cattle call.

So far I have found 3 properties that I think I would have a fair chance of getting offers accepted on.