Their loss is our gain.

Laws are now passed that prevent you from renting to yourself and claiming all the losses.

The conversation, as well as this decision, left me wondering how many insureds are denied policy coverage and cannot afford to bring a suit against the insurer and are unable to recover their loss.

I believe it tends to give me a slightly lower return, because the sponsor is going to be more careful, and if there is a severe downturn will prevent me from taking catastrophic losses.

If you want 100% of your investments in public equity, that is fine and you will reap those rewards or suffer those losses.  

Without a permit, the rental income might not need to be reported, but this approach risks legal issues, loss of tax benefits, and complications during audits or resale.

We’ve found a niche area that fits our budget and personal vision, and it has usually taken a few months of regularly analyzing deals to find something that works for us.

However, if you know and have a relationship with the person/team that will be doing the rehab for you in your absence and trust they have your vision in mind then you are in a better place to start. 

I wouldn't worry too much about it, if you have a competent CPA or bookkeeper they should be able to review your books and within minutes have a strong grasp on who gets a 1099 (spoiler alert, not every contractor gets one, I'll be annoyed if I get one since I'm structured as an S corporation) and the amounts to report.1099 filings are usually a loss leader for us, so if you're working with a professional make sure you take advantage of them filing everything for you.

I am not sure if it was just my market or more on their end but at the end it was a pretty big loss for us, so we cut it.