Historically, full service management on the coast has been costly but in recent months management rates have come down and quality has improved.

We also have a bank account at a smaller Chicago community bank, but there technology isn't as good to be honest.I think @Jonathan Greene's main point is don't step over dollars to pick up pennies. 

Historically this property has cashflowed, but not yielding an annual amount that's really making a high impact towards overall business growth ~12k per year.

I will provide some thoughts on the San Diego purchase- virtually all high LTV mls purchases since rates started to hike have negative cash flow at purchase- historically great appreciation- historically great rent growth but recently flattening- prop 13 is great benefit for long holds- laws keep getting less LL friendly.

Historically, we net roughly 65K Californians annually. 

Then you need to bid fair market value, not appropriate the bid to take into account the STR revenue but more so LTR.

They love the nostalgia of it and wouldn't consider replacing such an important and historical thing.There is no script that will lead you to success in this, but friendly and collaborative will help.

You can also split the difference by looking at the historic energy usage for the property and setting that as a utility 'cap.'

[1]    You might want to think about opening 2 FDIC insured savings accounts that have no fees.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.