My wife and I are looking at buying a property that we can live in and fix up (cosmetically) and then either rent it out as a standard SFH or as a short term rental. 

I have struggled over the past year getting financing for this project. 

So I would like to get ideas and thoughts here who has bought property with tenants already in there?

Yes, this is as niche as it gets, so odds are slim, but I'm curious to hear if anyone else lives on some acreage while boarding other horses on your property?

It ensures that when potential clients think of buying, selling, or renting property, your brand comes to mind first.

However, due to it being:1) In the state of California2) A shared home, rather than an outright external property being rented...the default insurance company on offer advised that many carriers are pulling out of CA and that I should go to a local insurance agency.My current insurance for home policy does not offer a "home-sharing endorsement" but only a separate renter's insurance, which would complicate things, since it's for traveling professionals, and they're not going to be booking for 12 straight months.

I’m looking to house hack my first property and walked through a couple of properties that have a fair amount of square footage but only 3 bedrooms.

A rule of thumb I use to advise my clients is: 1) the loan guarantee is worth 20-25% of the deal, 2) finding and vetting the deal is worth 25%, 3) executing the business plan for the property is worth 25% (i.e., overseeing contractors/property managers, etc.), and 4) contributing the money is worth 25-30%.

Either way, it doesn't make logical sense for the IRS to allow them the $500k married exclusion on both properties.

We have a handful of properties in the cape coral area that we're trying to find cheaper insurance coverage for.