This property is in the mountains and has electric heat, so the main bill comes in the winter when the heat is running.  

Yes, its mainly ordinary income from interest payments.

Mainly the Brokerage is for me just to sell the properties that we fix and flip and save the commission.

It's also worth noting that, given my community development background, the intent is to help them refi into traditional financing after they've established a payment history.

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

I'm fine with doing some minor fixes and improvements to a property: Adding overhead lighting/fans, better flooring, maybe redoing a main bathroom.

there was a group of 8 of us that pooled money in a Cabal myself and one other were the main money guys the others put in smaller amounts and when we won one.. we would divy up interest prorata to the amount contributed.. this kept those guys from competing against us and for sure we bid up newbies .. really the only ones that would beat us were those that wanted to live in the house and would just go almost all the way to retail or above .. or someone bidding on a second thinking it was a first and no one is going to help you if you dont know what your doing.. this is a very caveat emptar bizz.

Please note that I'm more active on my main socials, not here, so it may be a bit before I see your message.Have a killer week!

Compliance costs can really make it though for a startup if you don't intent to explode.

Main question in other countries is ownership and taxes.