Income is $600,000 per year and husband and wife both work full-time non real estate jobs.Is it true that the tax benefits are greater, or realized more quickly, on purchases like furniture or televisions to itemize a rental property, when they are made AFTER the date the property is put in service?

It worked, I got a few deals that way after awhile, but there are more efficient ways to market if you have more capital to work with like PPC or hiring VAs for lead generation.I'd still advise that if you're just getting into business, I would start slowly in terms of marketing spend.

I also learned that Furnished Finders is a great marketing site for mid-term rentals.

The area is growing significantly, and thus has what I believe is long term appreciating potential. 

You could ask your sister to finance it (her price, your terms).

I'd say the biggest benefit would be the fact that you can call him and he will help you through a deal.

The truth is that any business can lose money in the short term and long term. 

.- Hawaii property tax and insurance is considerably "okay"- Each Florida city has its own different trajectory in terms of appreciation, but HI appreciation depends on island and the town.- With most job now is being done remotely, especially in tech, Hawaii is becoming a viable choice.- However, the thing that makes Hawaii very doable is that the cost of flying is cheap, from CA one way the cost is $90-$200 depending on the season. - Every Hawaiian Island is very different from one to another, and between towns is also a bit different.

or is that just the generic term?

Here is what the offering circular with the sec says:Important terms of the Notes include the following, each of which is described in detail in this Offering Circular: •The Notes are unsecured, general recourse obligations of the Company that will be repaid from the Company’s working capital.