Given our financial constraints at the time, we couldn't afford such a high sum for limited coverage.I'm told that the lapse in coverage for the few months between being dropped by our previous insurer and attempting to get a landlord/investment property policy will make if VERY difficult to get a policy.I'm not sure that my agent really has much experience in insuring investment properties/rental properties.I reached out to Arcana (now MSI, and they forwarded my a list of agents/reps that could work with me.My question is: Are there any other places I should be looking to obtain coverage?

However, a challenging situation has arisen: the previous owner's son, who lost the house to the bank, is currently occupying it.I've attempted various methods to facilitate a smooth transition, including offering cash for keys and assistance with moving expenses.

Hey @Octa Sua, With all due respect, you are not ready to do a deal, so please DO NOT attempt to get anything under contract at this time.I don't mind jumping on a quick call to explain more about how the whole process works.

An attorney can attempt to file a TRO but again, what is their claim?

Even banks won’t attempt to do it.

I'm sure you'd like it to continue there, because you're trying to backpedal now by attempting to move the conversation out of the place where everyone can see it. 

I will attempt to reply with additional pics.

With current prices and interest rates, I would not attempt to jump into the STR game in a busy market unless that sub-market is showing abnormal YoY growth OR you have a solid plan to perform in the top 10% of current listings in that market, assuming the revenue pencils out.

As far as privacy you could list the property on MLS as a one time showing with a highest and best bid price, but no matter what you are going to come across people who say cash, but attempt to come to the table with a conventional, FHA or DSCR loan (personal experience). 

The lender did mention to me the alternative of putting the other 80K (put 20% DP instead of 40% DP in an attempt to offset negative cash flow) in a High yield saving account (currently @ 4.5%).