Besides attending to the myriad of questions, requests, and issues with tenants and the property, a good PM will provide liability protection with legal knowledge, asset protection with a tight lease, and increased ROI with simply smart management. 

Lastly in some areas, Maryland for example, if a property owner redeems, they must reimburse your legal fees.

Good taste - It is very inexpensive to paint and we have flippers who'd make world class designers.   

I live in the Bay Area of California, where I work in tech, particularly in hardware design and manufacturing - and have a huge passion for Virtual and Augmented Reality - it is the next wave of computing - and yes - I'm a bit of a recovering tech geek.

Also, if you can, get a second job or some kind of side hustle (legal of course, like cleaning common areas, cutting hair, cleaning homes, etc.) and use that money solely for paying of debt OR saving for a down-payment, making sure you put it in a high-yield savings account, so it can grow interest while it sits in there......no taking anything out of it. 

Do not rely on it for legal advice.

I would find a JV form on here and agree to terms and then spend a few hundered dollars getting a lawyer to do make it official and legal for your state.

2) What are the pros and cons of designating the home a second home versus an investment property?

The engineers' opinion initially should speak to the severity of the issue.I'd break down an engineering engagement into 2 parts:First would be an initial visit and rendering an opinion on the severity and possible approaches in design to remedy.2nd would be the actual design and cost opinion(s) to remedy.If you're pretty serious about the house, I think if you pay the $250-500 that I think you'd likely need to do the first, that would be a GREAT investment more than likely from what you're describing. 

How do I get the money LEGALLY?