Since you’re planning a mix of long-term and short-term rentals, keeping detailed records and setting up a solid system for managing finances early on will be key.

Changing careers can certainly be a challenge, but it sounds like you're equipped with a solid foundation thanks to your sister's support.

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

Thank you all for your responses.

Work with a real estate attorney to draft a formal agreement that outlines responsibilities and protects both parties. 

Thank you everyone for your very thoughtful and insightful responses.

A big part of the puzzle is making sure you run a solid cash flow analysis.

For investors focused on socially responsible projects, this balance can attract support from communities and municipalities.5.

The dude was solid. 

@V.G Jason @River Sava @Lisa Jones @Ben Pileggi @Gregory Schwartz @Jay HinrichsAnother silver lining I forgot to mention - Good investing partners.Having solid partners who can share the load (financially or logistically) during disasters can make a massive difference.