I do agree, this industry requires a lot of effort and if you put the work in, you will reap the rewards.

Specifically in NYC there is strategic value in having offices due to the advertising and financial industries. 

The main market I may focus on is Houston, because I have relatives there, and there are definitely opportunities within the rings of Houston.Currently, I am extremely busy with my construction business in OC, Ca, so the thought of OOS investing may have to postpone.I am actively investing in OC, Ca, and will probably sustain here for a while... because of the relationship I have developed with the colleagues in my construction industry.

My last bit of advice is be consistent most agents are out of the industry in under 2 years and it often takes months to get your first sale keep workin to generate leads, satisfy your clients, always keep your word and you'll be good to go.

I never heard or it discussed on the payback terms or what's the industry standard ....

It's a "too big to fail" industry that's indifferent to anti-landlord and anti-investor legislation ("ok, so we do more loans for primary residence owners, and less for investors, whatever"), adding a layer of safety.

While I have only been in the industry for 5 years now, people who are 30+ year industry veterans are saying this is the worse they have seen it.I think there are trends that people are not seeing to take advantage of, and it could be the darkest before the dawn moment, but it seems like there is no relief in sight for construction costs. 

They are forcing us to provide free service when no other industry in the US does this.

Do other homeowners insurance companies allow for one account to have different auto-payment setups for each property in the account, or is that not really a thing in this industry?

I'm not from the hair industry and had no idea how hard your job is until I became a salon owner.