You may have to search a bit for the right contractor or engineer - sometimes I see one solution dominating in an area - "that is how we always do it" 

Give me the horse and buggy vs a self driving car with immature software and sensors any day.My point is you should use as much technology as you can to make your life easier without going beyond its limits, and in the meantime always be on the lookout for new solutions that solve problems without creating new ones.

If you have a few single family rental homes and are looking for a way to streamline leases, applications and rents, maybe rentredi is the right solution, but if you have a multi unit property or any serious management needs, look elsewhere. 

There are hundreds of hard money lenders out there, ultimately I'd work with someone who has time to focus on ensuring you get a tailored mortgage instead of a cookie cutter solution.

CA is brutal when it comes to taxes.I don't give tax or legal advice, but many people believe that holding the property in your name and having a good umbrella policy is a good solution.

I'm all about finding problems to solutions and figuring out how to make something work rather than simply conceding that it cannot work.

Offer to buy them a few indoor portable heaters until you find a solution. 

Your goal is to plant the idea in their mind and create a situation where selling to you feels like the easiest and most logical solution for them.If you haven’t already, the first step is to get pre-approved for a mortgage so you know what you could afford if you were to purchase the property conventionally.

What are the biggest challenges people have faced with this. Also how do I make sure to get good tenants?

For example, incorporating energy-efficient solutions and smart home technology has been a game-changer in similar markets, especially when paired with features like office spaces that cater to remote workers.As for potential add-ons, corporate housing partnerships are a brilliant suggestion!